NPASS Compound

Structure

NPC268170 OpenBabel07101719252D 30 35 0 0 1 0 0 0 0 0999 V2000 3.2823 -0.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2766 -1.4217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0395 -0.7751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3353 -1.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7042 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8168 1.6263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8168 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4726 0.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8609 0.2089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1126 1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1126 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5210 1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5210 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9195 0.5462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7042 1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4084 1.6263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1567 1.7267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4084 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9494 1.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7042 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1567 -0.1004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.6263 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4084 2.6263 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9342 2.7016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4084 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9093 1.8262 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 10 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 30 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 29 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 0 0 0 0 18 25 2 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 1 1 6 0 0 0 27 30 2 0 0 0 0 28 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	423.08
Volume:	396.248
LogP:	2.574
LogD:	1.878
LogS:	-5.997
# Rotatable Bonds:	0
TPSA:	110.85
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	4.606
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.546
MDCK Permeability:	2.252156991744414e-05
Pgp-inhibitor:	0.733
Pgp-substrate:	0.473
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.223
30% Bioavailability (F30%):	0.736

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	81.40792083740234%
Volume Distribution (VD):	1.719
Pgp-substrate:	22.107606887817383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.671
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.506
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.497
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	0.65
Half-life (T1/2):	0.037

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.383
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.271
Rat Oral Acute Toxicity:	0.775
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.233
Carcinogencity:	0.436
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.3

Download Data

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

Natural Product: NPC268170

Natural Product ID:	NPC268170
*Common Name:**	Adociaquinone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KJMXEMKLXNMFIG-QFIPXVFZSA-N
Standard InCHI:	InChI=1S/C22H17NO6S/c1-22-4-2-3-10-9-29-20(15(10)22)18(25)13-7-11-12(8-14(13)22)19(26)21-16(17(11)24)23-5-6-30(21,27)28/h7-9,23H,2-6H2,1H3/t22-/m0/s1
SMILES:	C[C@]12CCCc3coc(c23)C(=O)c2cc3c(cc12)C(=O)C1=C(C3=O)NCCS1(=O)=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476648
PubChem CID:	11201041
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	13
Others	3

Activity Type	# Activity
Cell Line	5
Individual Protein	7
Others	1
Protein Family	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	21000.0	nM	PMID[529769]
NPT6399	Cell Line	XRS6	Cricetulus griseus	IC50	=	23000.0	nM	PMID[529769]
NPT5376	Individual Protein	DNA topoisomerase II	Drosophila melanogaster	IC90	=	78000.0	nM	PMID[529769]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	26000.0	nM	PMID[529770]
NPT1497	Individual Protein	Dual specificity protein phosphatase 1	Mus musculus	IC50	=	1100.0	nM	PMID[529770]
NPT1498	Individual Protein	Dual specificity protein phosphatase 6	Rattus norvegicus	IC50	=	1530.0	nM	PMID[529770]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	2900.0	nM	PMID[529773]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	6100.0	nM	PMID[529773]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	IC90	<	11000.0	nM	PMID[529769]
NPT2	Others	Unspecified		Ratio	=	3.0	n.a.	PMID[529769]
NPT911	Individual Protein	Dual specificity phosphatase Cdc25B	Homo sapiens	IC50	=	80.0	nM	PMID[529770]
NPT911	Individual Protein	Dual specificity phosphatase Cdc25B	Homo sapiens	IC50	=	110.0	nM	PMID[529770]
NPT911	Individual Protein	Dual specificity phosphatase Cdc25B	Homo sapiens	IC50	=	70.0	nM	PMID[529771]
NPT911	Individual Protein	Dual specificity phosphatase Cdc25B	Homo sapiens	IC50	=	70.0	nM	PMID[529772]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	200.0	nM	PMID[529773]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	4600.0	nM	PMID[529773]

☑ 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 NPC268170 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	315
0.1-0.2	2074
0.2-0.3	6911
0.3-0.4	11538
0.4-0.5	10502
0.5-0.6	10978
0.6-0.7	366
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC93574
0.9615	High Similarity	NPC255861
0.9392	High Similarity	NPC163867
0.8457	Intermediate Similarity	NPC472358
0.7958	Intermediate Similarity	NPC472533
0.774	Intermediate Similarity	NPC114513
0.774	Intermediate Similarity	NPC245522
0.7403	Intermediate Similarity	NPC478166
0.7377	Intermediate Similarity	NPC192069
0.7312	Intermediate Similarity	NPC282793
0.7181	Intermediate Similarity	NPC88958
0.7181	Intermediate Similarity	NPC469966
0.7	Intermediate Similarity	NPC23559
0.6989	Remote Similarity	NPC281398
0.6931	Remote Similarity	NPC144010
0.6911	Remote Similarity	NPC179170
0.6895	Remote Similarity	NPC145830
0.6869	Remote Similarity	NPC473945
0.6828	Remote Similarity	NPC117674
0.6823	Remote Similarity	NPC25351
0.6791	Remote Similarity	NPC27798
0.6791	Remote Similarity	NPC93241
0.6771	Remote Similarity	NPC10429
0.6768	Remote Similarity	NPC472784
0.6753	Remote Similarity	NPC221992
0.6702	Remote Similarity	NPC290038
0.67	Remote Similarity	NPC44602
0.6684	Remote Similarity	NPC27615
0.6667	Remote Similarity	NPC157958
0.6667	Remote Similarity	NPC233763
0.6667	Remote Similarity	NPC313582
0.6649	Remote Similarity	NPC95526
0.6649	Remote Similarity	NPC265181
0.6649	Remote Similarity	NPC233707
0.6633	Remote Similarity	NPC299094
0.6633	Remote Similarity	NPC10051
0.663	Remote Similarity	NPC307401
0.6615	Remote Similarity	NPC478159
0.6615	Remote Similarity	NPC478161
0.6615	Remote Similarity	NPC472298
0.6612	Remote Similarity	NPC324117
0.6597	Remote Similarity	NPC478163
0.6595	Remote Similarity	NPC177262
0.6588	Remote Similarity	NPC174783
0.6577	Remote Similarity	NPC478048
0.657	Remote Similarity	NPC214629
0.6569	Remote Similarity	NPC167340
0.6566	Remote Similarity	NPC472781
0.6566	Remote Similarity	NPC472782
0.6559	Remote Similarity	NPC202260
0.6556	Remote Similarity	NPC59502
0.6548	Remote Similarity	NPC472823
0.6547	Remote Similarity	NPC180210
0.6547	Remote Similarity	NPC314914
0.6547	Remote Similarity	NPC328856
0.6547	Remote Similarity	NPC478047
0.6547	Remote Similarity	NPC321226
0.6547	Remote Similarity	NPC478046
0.6545	Remote Similarity	NPC470019
0.6544	Remote Similarity	NPC126211
0.6543	Remote Similarity	NPC263337
0.6535	Remote Similarity	NPC302392
0.6533	Remote Similarity	NPC472783
0.6533	Remote Similarity	NPC476035
0.6533	Remote Similarity	NPC475039
0.6533	Remote Similarity	NPC170101
0.6533	Remote Similarity	NPC14499
0.6533	Remote Similarity	NPC472780
0.6526	Remote Similarity	NPC2672
0.6522	Remote Similarity	NPC209858
0.6518	Remote Similarity	NPC316368
0.6518	Remote Similarity	NPC284236
0.6513	Remote Similarity	NPC44606
0.6512	Remote Similarity	NPC311781
0.6505	Remote Similarity	NPC186647
0.6481	Remote Similarity	NPC67346
0.6477	Remote Similarity	NPC474107
0.6477	Remote Similarity	NPC472839
0.6465	Remote Similarity	NPC123153
0.6461	Remote Similarity	NPC178382
0.6458	Remote Similarity	NPC71821
0.6453	Remote Similarity	NPC472894
0.6442	Remote Similarity	NPC149571
0.6436	Remote Similarity	NPC41689
0.6436	Remote Similarity	NPC473766
0.6436	Remote Similarity	NPC473753
0.6432	Remote Similarity	NPC472299
0.6429	Remote Similarity	NPC471863
0.6425	Remote Similarity	NPC115906
0.6422	Remote Similarity	NPC4669
0.6417	Remote Similarity	NPC290601
0.6414	Remote Similarity	NPC7059
0.641	Remote Similarity	NPC472787
0.6406	Remote Similarity	NPC140577
0.6406	Remote Similarity	NPC97086
0.6406	Remote Similarity	NPC43069
0.64	Remote Similarity	NPC471003
0.6398	Remote Similarity	NPC217914
0.6396	Remote Similarity	NPC472786
0.6396	Remote Similarity	NPC75310
0.639	Remote Similarity	NPC469964
0.639	Remote Similarity	NPC476236
0.639	Remote Similarity	NPC472474
0.6387	Remote Similarity	NPC199044
0.6387	Remote Similarity	NPC238843
0.6386	Remote Similarity	NPC475779
0.6382	Remote Similarity	NPC473368
0.6381	Remote Similarity	NPC329790
0.6378	Remote Similarity	NPC471613
0.6378	Remote Similarity	NPC189773
0.6373	Remote Similarity	NPC88593
0.6364	Remote Similarity	NPC104736
0.6364	Remote Similarity	NPC471670
0.6364	Remote Similarity	NPC41880
0.6359	Remote Similarity	NPC239134
0.6359	Remote Similarity	NPC164295
0.6359	Remote Similarity	NPC279596
0.6359	Remote Similarity	NPC316164
0.6359	Remote Similarity	NPC212257
0.6359	Remote Similarity	NPC228842
0.6354	Remote Similarity	NPC185456
0.6354	Remote Similarity	NPC472836
0.635	Remote Similarity	NPC287559
0.635	Remote Similarity	NPC8389
0.6349	Remote Similarity	NPC18904
0.634	Remote Similarity	NPC252208
0.6332	Remote Similarity	NPC304692
0.6332	Remote Similarity	NPC81405
0.633	Remote Similarity	NPC232533
0.6329	Remote Similarity	NPC121400
0.6327	Remote Similarity	NPC272590
0.6324	Remote Similarity	NPC293253
0.6324	Remote Similarity	NPC298071
0.6321	Remote Similarity	NPC62799
0.6321	Remote Similarity	NPC262198
0.6321	Remote Similarity	NPC471292
0.6319	Remote Similarity	NPC476917
0.6319	Remote Similarity	NPC327527
0.6318	Remote Similarity	NPC476569
0.6318	Remote Similarity	NPC79571
0.6313	Remote Similarity	NPC476443
0.6313	Remote Similarity	NPC472785
0.6313	Remote Similarity	NPC133817
0.6313	Remote Similarity	NPC41719
0.631	Remote Similarity	NPC307682
0.631	Remote Similarity	NPC22644
0.6308	Remote Similarity	NPC280025
0.6305	Remote Similarity	NPC132054
0.6305	Remote Similarity	NPC308156
0.6305	Remote Similarity	NPC277618
0.6302	Remote Similarity	NPC53016
0.6302	Remote Similarity	NPC472840
0.6302	Remote Similarity	NPC158871
0.63	Remote Similarity	NPC140952
0.63	Remote Similarity	NPC475780
0.6294	Remote Similarity	NPC246164
0.6294	Remote Similarity	NPC475777
0.6294	Remote Similarity	NPC121615
0.6294	Remote Similarity	NPC294511
0.6293	Remote Similarity	NPC227683
0.6293	Remote Similarity	NPC472660
0.6292	Remote Similarity	NPC97566
0.629	Remote Similarity	NPC470406
0.6289	Remote Similarity	NPC250331
0.6289	Remote Similarity	NPC224418
0.6284	Remote Similarity	NPC208389
0.6281	Remote Similarity	NPC3898
0.6276	Remote Similarity	NPC226578
0.6275	Remote Similarity	NPC279768
0.6275	Remote Similarity	NPC316262
0.6275	Remote Similarity	NPC314653
0.6269	Remote Similarity	NPC308006
0.6269	Remote Similarity	NPC250076
0.6269	Remote Similarity	NPC56731
0.6268	Remote Similarity	NPC298339
0.6263	Remote Similarity	NPC470407
0.6263	Remote Similarity	NPC56197
0.6263	Remote Similarity	NPC218204
0.6263	Remote Similarity	NPC148374
0.6263	Remote Similarity	NPC61157
0.6263	Remote Similarity	NPC473681
0.6263	Remote Similarity	NPC24232
0.6262	Remote Similarity	NPC20734
0.6257	Remote Similarity	NPC474659
0.6256	Remote Similarity	NPC243483
0.625	Remote Similarity	NPC276231
0.625	Remote Similarity	NPC201297
0.625	Remote Similarity	NPC476925
0.625	Remote Similarity	NPC288353
0.625	Remote Similarity	NPC472283
0.6244	Remote Similarity	NPC473245
0.6244	Remote Similarity	NPC255787
0.6244	Remote Similarity	NPC58661
0.6244	Remote Similarity	NPC191012
0.6244	Remote Similarity	NPC291742
0.6244	Remote Similarity	NPC176304
0.6244	Remote Similarity	NPC314946
0.6244	Remote Similarity	NPC70840
0.6243	Remote Similarity	NPC471996
0.6243	Remote Similarity	NPC301341

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 NPC268170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	845
0.2-0.3	1016
0.3-0.4	2497
0.4-0.5	3045
0.5-0.6	1473
0.6-0.7	84
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
0.7234	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5564	Approved
0.6849	Remote Similarity	NPD5980	Discovery
0.6701	Remote Similarity	NPD5262	Discontinued
0.67	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6250	Discontinued
0.6649	Remote Similarity	NPD1471	Phase 3
0.6636	Remote Similarity	NPD7627	Approved
0.6636	Remote Similarity	NPD7626	Approved
0.662	Remote Similarity	NPD4107	Approved
0.6618	Remote Similarity	NPD7693	Approved
0.6591	Remote Similarity	NPD5480	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6764	Approved
0.6569	Remote Similarity	NPD6765	Approved
0.6546	Remote Similarity	NPD5889	Approved
0.6546	Remote Similarity	NPD5890	Approved
0.6535	Remote Similarity	NPD7177	Discontinued
0.6535	Remote Similarity	NPD2163	Approved
0.6513	Remote Similarity	NPD5356	Approved
0.6513	Remote Similarity	NPD5355	Approved
0.6512	Remote Similarity	NPD4482	Phase 3
0.6509	Remote Similarity	NPD3659	Discontinued
0.6502	Remote Similarity	NPD4503	Phase 2
0.6497	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4505	Phase 1
0.6484	Remote Similarity	NPD4859	Phase 1
0.6481	Remote Similarity	NPD3057	Approved
0.6456	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3752	Phase 2
0.6443	Remote Similarity	NPD2649	Approved
0.6443	Remote Similarity	NPD2651	Approved
0.6442	Remote Similarity	NPD6989	Approved
0.6442	Remote Similarity	NPD6990	Approved
0.6425	Remote Similarity	NPD2968	Approved
0.6425	Remote Similarity	NPD2971	Approved
0.6422	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD2531	Phase 2
0.641	Remote Similarity	NPD6585	Discontinued
0.6406	Remote Similarity	NPD2972	Approved
0.6406	Remote Similarity	NPD3533	Approved
0.6387	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7162	Approved
0.6382	Remote Similarity	NPD1309	Phase 2
0.6382	Remote Similarity	NPD1307	Phase 2
0.6381	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6834	Approved
0.635	Remote Similarity	NPD5709	Phase 3
0.634	Remote Similarity	NPD2900	Approved
0.634	Remote Similarity	NPD2901	Approved
0.6333	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2491	Approved
0.6323	Remote Similarity	NPD5676	Approved
0.6318	Remote Similarity	NPD4666	Phase 3
0.6316	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5025	Approved
0.6275	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD8285	Discontinued
0.6263	Remote Similarity	NPD6280	Approved
0.6263	Remote Similarity	NPD6279	Approved
0.6256	Remote Similarity	NPD3448	Approved
0.6256	Remote Similarity	NPD6808	Phase 2
0.6256	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7038	Approved
0.625	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7039	Approved
0.6244	Remote Similarity	NPD2490	Approved
0.6244	Remote Similarity	NPD2488	Approved
0.6237	Remote Similarity	NPD3140	Approved
0.6237	Remote Similarity	NPD4661	Approved
0.6237	Remote Similarity	NPD3142	Approved
0.6237	Remote Similarity	NPD4662	Approved
0.6223	Remote Similarity	NPD8469	Approved
0.622	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6677	Suspended
0.6188	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD8404	Phase 2
0.6181	Remote Similarity	NPD6844	Discontinued
0.6181	Remote Similarity	NPD7577	Discontinued
0.6176	Remote Similarity	NPD7229	Phase 3
0.6175	Remote Similarity	NPD2973	Approved
0.6175	Remote Similarity	NPD2974	Approved
0.6175	Remote Similarity	NPD2975	Approved
0.6173	Remote Similarity	NPD7427	Discontinued
0.6173	Remote Similarity	NPD4727	Phase 1
0.6171	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4981	Phase 2
0.6169	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6776	Approved
0.6164	Remote Similarity	NPD6777	Approved
0.6164	Remote Similarity	NPD6780	Approved
0.6164	Remote Similarity	NPD6782	Approved
0.6164	Remote Similarity	NPD6778	Approved
0.6164	Remote Similarity	NPD6779	Approved
0.6164	Remote Similarity	NPD6781	Approved
0.6157	Remote Similarity	NPD6871	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD1891	Discontinued
0.6136	Remote Similarity	NPD6321	Discontinued
0.6131	Remote Similarity	NPD6873	Phase 2
0.6126	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD8311	Discontinued
0.6119	Remote Similarity	NPD5978	Approved
0.6119	Remote Similarity	NPD5977	Approved
0.6117	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5950	Discontinued
0.6114	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6181	Discontinued
0.6108	Remote Similarity	NPD6862	Phase 2
0.6106	Remote Similarity	NPD6042	Phase 2
0.6106	Remote Similarity	NPD42	Phase 2
0.6103	Remote Similarity	NPD8434	Phase 2
0.6096	Remote Similarity	NPD7713	Phase 3
0.6091	Remote Similarity	NPD3873	Phase 3
0.6091	Remote Similarity	NPD5457	Discontinued
0.6091	Remote Similarity	NPD4580	Approved
0.6091	Remote Similarity	NPD3869	Phase 3
0.6085	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD7698	Approved
0.6081	Remote Similarity	NPD7697	Approved
0.6081	Remote Similarity	NPD7696	Phase 3
0.6078	Remote Similarity	NPD7907	Approved
0.6075	Remote Similarity	NPD7291	Discontinued
0.6073	Remote Similarity	NPD4476	Approved
0.6073	Remote Similarity	NPD4477	Approved
0.6071	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD2493	Approved
0.6063	Remote Similarity	NPD2494	Approved
0.6062	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6620	Discovery
0.6056	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD4040	Phase 1
0.6054	Remote Similarity	NPD7871	Phase 2
0.6054	Remote Similarity	NPD7870	Phase 2
0.605	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5953	Discontinued
0.6045	Remote Similarity	NPD3297	Approved
0.6043	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD6273	Approved
0.6041	Remote Similarity	NPD5049	Phase 3
0.6034	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD7003	Approved
0.603	Remote Similarity	NPD3226	Approved
0.6029	Remote Similarity	NPD6315	Phase 2
0.6028	Remote Similarity	NPD4434	Approved
0.6027	Remote Similarity	NPD8161	Suspended
0.6026	Remote Similarity	NPD7278	Phase 2
0.6026	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD7279	Phase 2
0.6019	Remote Similarity	NPD7668	Phase 2
0.6019	Remote Similarity	NPD1298	Discontinued
0.6018	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.601	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.601	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.601	Remote Similarity	NPD2897	Discontinued
0.601	Remote Similarity	NPD6031	Approved
0.601	Remote Similarity	NPD6030	Approved
0.6009	Remote Similarity	NPD6535	Approved
0.6009	Remote Similarity	NPD7435	Discontinued
0.6009	Remote Similarity	NPD6534	Approved
0.6009	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD8366	Approved
0.6	Remote Similarity	NPD1559	Discontinued
0.6	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4435	Approved
0.6	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD4111	Phase 1
0.5991	Remote Similarity	NPD4665	Approved
0.5991	Remote Similarity	NPD3450	Approved
0.5991	Remote Similarity	NPD3452	Approved
0.5982	Remote Similarity	NPD4583	Approved
0.5982	Remote Similarity	NPD3298	Approved
0.5982	Remote Similarity	NPD4582	Approved
0.5979	Remote Similarity	NPD3373	Approved
0.5979	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD3250	Phase 1
0.5975	Remote Similarity	NPD8491	Approved
0.5973	Remote Similarity	NPD7701	Phase 2
0.5973	Remote Similarity	NPD7391	Discontinued
0.5972	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD1247	Approved
0.597	Remote Similarity	NPD6385	Approved
0.597	Remote Similarity	NPD6386	Approved
0.5969	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8152	Approved
0.5968	Remote Similarity	NPD8153	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