NPASS Compound

Structure

NPC470560 OpenBabel07101718222D 29 31 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 29 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 6 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 17 2 0 0 0 0 13 29 1 0 0 0 0 14 19 1 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 25 2 0 0 0 0 19 26 2 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.1
Volume:	401.754
LogP:	5.93
LogD:	2.733
LogS:	-3.448
# Rotatable Bonds:	6
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.165
Synthetic Accessibility Score:	2.958
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.158
MDCK Permeability:	1.366139895253582e-05
Pgp-inhibitor:	0.122
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.802
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	98.5082778930664%
Volume Distribution (VD):	0.463
Pgp-substrate:	3.7571325302124023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.745
CYP1A2-substrate:	0.437
CYP2C19-inhibitor:	0.268
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.786
CYP2C9-substrate:	0.586
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	4.866
Half-life (T1/2):	0.487

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.629
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.821
Skin Sensitization:	0.939
Carcinogencity:	0.126
Eye Corrosion:	0.003
Eye Irritation:	0.916
Respiratory Toxicity:	0.264

Download Data

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

Natural Product: NPC470560

Natural Product ID:	NPC470560
*Common Name:**	(-)-(1's)-6-O-Methyl-7-Chloroaverantin
IUPAC Name:	2-chloro-1,6,8-trihydroxy-7-[(1S)-1-hydroxyhexyl]-3-methoxyanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	KRLUFPHVSFXHOK-NSHDSACASA-N
Standard InCHI:	InChI=1S/C21H21ClO7/c1-3-4-5-6-11(23)16-12(24)7-9-14(20(16)27)19(26)15-10(18(9)25)8-13(29-2)17(22)21(15)28/h7-8,11,23-24,27-28H,3-6H2,1-2H3/t11-/m0/s1
SMILES:	CCCCC[C@@H](c1c(O)cc2c(c1O)C(=O)c1c(C2=O)cc(c(c1O)Cl)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071279
PubChem CID:	60199737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	7110.0	nM	PMID[489416]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6640.0	nM	PMID[489416]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	7420.0	nM	PMID[489416]

☑ 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 NPC470560 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	458
0.1-0.2	2018
0.2-0.3	4943
0.3-0.4	12257
0.4-0.5	6150
0.5-0.6	5490
0.6-0.7	6447
0.7-0.8	4692
0.8-0.85	172
0.85-0.9	56
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC470562
0.9691	High Similarity	NPC470565
0.9563	High Similarity	NPC470561
0.9503	High Similarity	NPC470563
0.9375	High Similarity	NPC470559
0.9281	High Similarity	NPC264922
0.9277	High Similarity	NPC474857
0.9217	High Similarity	NPC277865
0.9012	High Similarity	NPC470564
0.8914	High Similarity	NPC316091
0.8882	High Similarity	NPC470569
0.882	High Similarity	NPC470568
0.8807	High Similarity	NPC313386
0.8786	High Similarity	NPC306240
0.8722	High Similarity	NPC313541
0.8704	High Similarity	NPC290954
0.8704	High Similarity	NPC147735
0.8704	High Similarity	NPC255641
0.8693	High Similarity	NPC191606
0.8671	High Similarity	NPC45072
0.8663	High Similarity	NPC470422
0.8634	High Similarity	NPC289042
0.8634	High Similarity	NPC118027
0.8634	High Similarity	NPC245584
0.8634	High Similarity	NPC126767
0.8634	High Similarity	NPC56433
0.8634	High Similarity	NPC190648
0.8634	High Similarity	NPC312929
0.8629	High Similarity	NPC151292
0.8598	High Similarity	NPC154683
0.8598	High Similarity	NPC40356
0.8529	High Similarity	NPC68850
0.8509	High Similarity	NPC34482
0.8503	High Similarity	NPC197326
0.8476	Intermediate Similarity	NPC294646
0.8457	Intermediate Similarity	NPC470570
0.8452	Intermediate Similarity	NPC324736
0.8447	Intermediate Similarity	NPC48762
0.8447	Intermediate Similarity	NPC19896
0.8436	Intermediate Similarity	NPC474499
0.8434	Intermediate Similarity	NPC208806
0.843	Intermediate Similarity	NPC472032
0.8405	Intermediate Similarity	NPC34802
0.8395	Intermediate Similarity	NPC49282
0.8385	Intermediate Similarity	NPC167663
0.8383	Intermediate Similarity	NPC66508
0.8383	Intermediate Similarity	NPC226656
0.8333	Intermediate Similarity	NPC21599
0.8333	Intermediate Similarity	NPC193703
0.8323	Intermediate Similarity	NPC107109
0.8323	Intermediate Similarity	NPC135524
0.8313	Intermediate Similarity	NPC478148
0.8313	Intermediate Similarity	NPC46882
0.8313	Intermediate Similarity	NPC132990
0.8313	Intermediate Similarity	NPC232645
0.8313	Intermediate Similarity	NPC72958
0.8313	Intermediate Similarity	NPC474417
0.8313	Intermediate Similarity	NPC149526
0.8303	Intermediate Similarity	NPC329933
0.8284	Intermediate Similarity	NPC37543
0.8284	Intermediate Similarity	NPC199463
0.8282	Intermediate Similarity	NPC478019
0.8272	Intermediate Similarity	NPC84266
0.8263	Intermediate Similarity	NPC470337
0.8263	Intermediate Similarity	NPC113608
0.8263	Intermediate Similarity	NPC470338
0.8263	Intermediate Similarity	NPC470340
0.8263	Intermediate Similarity	NPC180944
0.8263	Intermediate Similarity	NPC268992
0.8263	Intermediate Similarity	NPC51824
0.8263	Intermediate Similarity	NPC87708
0.8261	Intermediate Similarity	NPC305845
0.8261	Intermediate Similarity	NPC204045
0.8256	Intermediate Similarity	NPC470081
0.8253	Intermediate Similarity	NPC202595
0.8242	Intermediate Similarity	NPC172329
0.8242	Intermediate Similarity	NPC2569
0.8229	Intermediate Similarity	NPC474004
0.8225	Intermediate Similarity	NPC5379
0.8225	Intermediate Similarity	NPC77807
0.8225	Intermediate Similarity	NPC14561
0.8222	Intermediate Similarity	NPC99937
0.8218	Intermediate Similarity	NPC472058
0.8218	Intermediate Similarity	NPC105414
0.8218	Intermediate Similarity	NPC470341
0.8218	Intermediate Similarity	NPC324522
0.8218	Intermediate Similarity	NPC234497
0.8214	Intermediate Similarity	NPC214632
0.8214	Intermediate Similarity	NPC155686
0.8214	Intermediate Similarity	NPC93552
0.821	Intermediate Similarity	NPC49108
0.821	Intermediate Similarity	NPC182255
0.821	Intermediate Similarity	NPC94076
0.8208	Intermediate Similarity	NPC472051
0.8208	Intermediate Similarity	NPC472057
0.8198	Intermediate Similarity	NPC473696
0.8193	Intermediate Similarity	NPC158338
0.8193	Intermediate Similarity	NPC97028
0.8193	Intermediate Similarity	NPC100985
0.8193	Intermediate Similarity	NPC65589
0.8193	Intermediate Similarity	NPC97029
0.8193	Intermediate Similarity	NPC288036
0.8192	Intermediate Similarity	NPC477568
0.8187	Intermediate Similarity	NPC472052
0.8187	Intermediate Similarity	NPC284495
0.8187	Intermediate Similarity	NPC472060
0.8187	Intermediate Similarity	NPC470342
0.8187	Intermediate Similarity	NPC470810
0.8176	Intermediate Similarity	NPC178976
0.8176	Intermediate Similarity	NPC474637
0.8176	Intermediate Similarity	NPC263483
0.8171	Intermediate Similarity	NPC470567
0.8171	Intermediate Similarity	NPC28632
0.8166	Intermediate Similarity	NPC68727
0.8161	Intermediate Similarity	NPC477835
0.816	Intermediate Similarity	NPC3732
0.815	Intermediate Similarity	NPC100849
0.8148	Intermediate Similarity	NPC253822
0.8144	Intermediate Similarity	NPC280295
0.8144	Intermediate Similarity	NPC225854
0.8142	Intermediate Similarity	NPC470099
0.814	Intermediate Similarity	NPC298401
0.8133	Intermediate Similarity	NPC472056
0.8133	Intermediate Similarity	NPC27221
0.8133	Intermediate Similarity	NPC256672
0.8133	Intermediate Similarity	NPC7025
0.8128	Intermediate Similarity	NPC154720
0.8121	Intermediate Similarity	NPC163846
0.8121	Intermediate Similarity	NPC225173
0.8121	Intermediate Similarity	NPC300540
0.8114	Intermediate Similarity	NPC470566
0.811	Intermediate Similarity	NPC475201
0.811	Intermediate Similarity	NPC471906
0.811	Intermediate Similarity	NPC51887
0.811	Intermediate Similarity	NPC475705
0.811	Intermediate Similarity	NPC117836
0.811	Intermediate Similarity	NPC476178
0.811	Intermediate Similarity	NPC244691
0.8107	Intermediate Similarity	NPC329844
0.8107	Intermediate Similarity	NPC135522
0.8107	Intermediate Similarity	NPC210942
0.8107	Intermediate Similarity	NPC169990
0.8101	Intermediate Similarity	NPC471802
0.8098	Intermediate Similarity	NPC321980
0.8098	Intermediate Similarity	NPC26051
0.8098	Intermediate Similarity	NPC474961
0.8098	Intermediate Similarity	NPC55832
0.8098	Intermediate Similarity	NPC268204
0.8098	Intermediate Similarity	NPC52789
0.8098	Intermediate Similarity	NPC470087
0.8095	Intermediate Similarity	NPC230848
0.8092	Intermediate Similarity	NPC474096
0.8092	Intermediate Similarity	NPC472059
0.8086	Intermediate Similarity	NPC470211
0.8086	Intermediate Similarity	NPC472366
0.8084	Intermediate Similarity	NPC10027
0.8084	Intermediate Similarity	NPC80370
0.8084	Intermediate Similarity	NPC65775
0.8081	Intermediate Similarity	NPC472618
0.8081	Intermediate Similarity	NPC84571
0.8079	Intermediate Similarity	NPC271385
0.8079	Intermediate Similarity	NPC5029
0.8079	Intermediate Similarity	NPC30432
0.8079	Intermediate Similarity	NPC111536
0.8079	Intermediate Similarity	NPC76128
0.8072	Intermediate Similarity	NPC125801
0.8072	Intermediate Similarity	NPC22005
0.8072	Intermediate Similarity	NPC123202
0.8072	Intermediate Similarity	NPC7943
0.807	Intermediate Similarity	NPC201127
0.8061	Intermediate Similarity	NPC476055
0.8057	Intermediate Similarity	NPC28669
0.8057	Intermediate Similarity	NPC474061
0.8054	Intermediate Similarity	NPC221185
0.8049	Intermediate Similarity	NPC277369
0.8049	Intermediate Similarity	NPC215451
0.8047	Intermediate Similarity	NPC273483
0.8047	Intermediate Similarity	NPC474843
0.8046	Intermediate Similarity	NPC472053
0.8043	Intermediate Similarity	NPC470100
0.8037	Intermediate Similarity	NPC144118
0.8037	Intermediate Similarity	NPC204985
0.8037	Intermediate Similarity	NPC219917
0.8037	Intermediate Similarity	NPC48624
0.8037	Intermediate Similarity	NPC213659
0.8037	Intermediate Similarity	NPC101366
0.8037	Intermediate Similarity	NPC259166
0.8037	Intermediate Similarity	NPC172250
0.8037	Intermediate Similarity	NPC326109
0.8037	Intermediate Similarity	NPC80962
0.8037	Intermediate Similarity	NPC215311
0.8036	Intermediate Similarity	NPC474660
0.8035	Intermediate Similarity	NPC311740
0.8034	Intermediate Similarity	NPC472054
0.8034	Intermediate Similarity	NPC98776
0.8025	Intermediate Similarity	NPC190457
0.8025	Intermediate Similarity	NPC242994
0.8025	Intermediate Similarity	NPC1268
0.8025	Intermediate Similarity	NPC138099
0.8023	Intermediate Similarity	NPC472617

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 NPC470560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	1100
0.2-0.3	1902
0.3-0.4	2790
0.4-0.5	1782
0.5-0.6	844
0.6-0.7	269
0.7-0.8	65
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
0.8035	Intermediate Similarity	NPD6959	Discontinued
0.795	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6232	Discontinued
0.7853	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7738	Intermediate Similarity	NPD2533	Approved
0.7738	Intermediate Similarity	NPD2532	Approved
0.7738	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD1510	Phase 2
0.7719	Intermediate Similarity	NPD4380	Phase 2
0.7716	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD2403	Approved
0.7593	Intermediate Similarity	NPD1240	Approved
0.759	Intermediate Similarity	NPD1549	Phase 2
0.753	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5844	Phase 1
0.7471	Intermediate Similarity	NPD7411	Suspended
0.7471	Intermediate Similarity	NPD7390	Discontinued
0.747	Intermediate Similarity	NPD2796	Approved
0.7458	Intermediate Similarity	NPD7075	Discontinued
0.7457	Intermediate Similarity	NPD3226	Approved
0.7429	Intermediate Similarity	NPD6801	Discontinued
0.7429	Intermediate Similarity	NPD1934	Approved
0.7386	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD4363	Phase 3
0.7382	Intermediate Similarity	NPD4360	Phase 2
0.7368	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6166	Phase 2
0.7308	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3882	Suspended
0.7303	Intermediate Similarity	NPD7768	Phase 2
0.7288	Intermediate Similarity	NPD2801	Approved
0.7278	Intermediate Similarity	NPD5494	Approved
0.7263	Intermediate Similarity	NPD3749	Approved
0.7263	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2935	Discontinued
0.7258	Intermediate Similarity	NPD6559	Discontinued
0.7254	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4361	Phase 2
0.7235	Intermediate Similarity	NPD2800	Approved
0.7228	Intermediate Similarity	NPD3818	Discontinued
0.7216	Intermediate Similarity	NPD6599	Discontinued
0.7207	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5710	Approved
0.7198	Intermediate Similarity	NPD5711	Approved
0.7193	Intermediate Similarity	NPD3750	Approved
0.7193	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6651	Approved
0.7168	Intermediate Similarity	NPD1511	Approved
0.716	Intermediate Similarity	NPD1470	Approved
0.7151	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2346	Discontinued
0.7107	Intermediate Similarity	NPD6782	Approved
0.7107	Intermediate Similarity	NPD6780	Approved
0.7107	Intermediate Similarity	NPD6776	Approved
0.7107	Intermediate Similarity	NPD6781	Approved
0.7107	Intermediate Similarity	NPD6777	Approved
0.7107	Intermediate Similarity	NPD6779	Approved
0.7107	Intermediate Similarity	NPD6778	Approved
0.7102	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1512	Approved
0.7079	Intermediate Similarity	NPD8151	Discontinued
0.7069	Intermediate Similarity	NPD6799	Approved
0.7062	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7074	Phase 3
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD6099	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD1551	Phase 2
0.7059	Intermediate Similarity	NPD5405	Approved
0.7039	Intermediate Similarity	NPD37	Approved
0.7021	Intermediate Similarity	NPD5953	Discontinued
0.7005	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD7696	Phase 3
0.7	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD7698	Approved
0.6995	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4628	Phase 3
0.6971	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7041	Phase 2
0.6968	Remote Similarity	NPD7472	Approved
0.6965	Remote Similarity	NPD7870	Phase 2
0.6965	Remote Similarity	NPD7871	Phase 2
0.6964	Remote Similarity	NPD943	Approved
0.6961	Remote Similarity	NPD3817	Phase 2
0.6961	Remote Similarity	NPD5402	Approved
0.6949	Remote Similarity	NPD920	Approved
0.6947	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6797	Phase 2
0.6931	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4967	Phase 2
0.6919	Remote Similarity	NPD2344	Approved
0.6915	Remote Similarity	NPD7286	Phase 2
0.6914	Remote Similarity	NPD1201	Approved
0.6906	Remote Similarity	NPD1465	Phase 2
0.6901	Remote Similarity	NPD3748	Approved
0.6901	Remote Similarity	NPD2799	Discontinued
0.6897	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7003	Approved
0.6895	Remote Similarity	NPD7251	Discontinued
0.6891	Remote Similarity	NPD8150	Discontinued
0.6872	Remote Similarity	NPD7458	Discontinued
0.6863	Remote Similarity	NPD7701	Phase 2
0.6862	Remote Similarity	NPD3751	Discontinued
0.6859	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7808	Phase 3
0.6857	Remote Similarity	NPD3887	Approved
0.6854	Remote Similarity	NPD5403	Approved
0.6853	Remote Similarity	NPD6534	Approved
0.6853	Remote Similarity	NPD6535	Approved
0.6848	Remote Similarity	NPD6234	Discontinued
0.6839	Remote Similarity	NPD1243	Approved
0.6836	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7874	Approved
0.6791	Remote Similarity	NPD3926	Phase 2
0.6786	Remote Similarity	NPD4625	Phase 3
0.6782	Remote Similarity	NPD6823	Phase 2
0.6776	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7801	Approved
0.6761	Remote Similarity	NPD2354	Approved
0.6761	Remote Similarity	NPD2309	Approved
0.676	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7700	Phase 2
0.675	Remote Similarity	NPD7699	Phase 2
0.6746	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5401	Approved
0.6738	Remote Similarity	NPD7229	Phase 3
0.6723	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2798	Approved
0.6705	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6273	Approved
0.6684	Remote Similarity	NPD1247	Approved
0.6684	Remote Similarity	NPD7228	Approved
0.6684	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD919	Approved
0.6649	Remote Similarity	NPD3787	Discontinued
0.6648	Remote Similarity	NPD1578	Phase 2
0.6647	Remote Similarity	NPD4538	Approved
0.6647	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2313	Discontinued
0.6647	Remote Similarity	NPD3764	Approved
0.6647	Remote Similarity	NPD4536	Approved
0.6634	Remote Similarity	NPD8320	Phase 1
0.6634	Remote Similarity	NPD8319	Approved
0.6633	Remote Similarity	NPD8434	Phase 2
0.6633	Remote Similarity	NPD6212	Phase 3
0.6633	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6213	Phase 3
0.663	Remote Similarity	NPD5760	Phase 2
0.663	Remote Similarity	NPD5761	Phase 2
0.6629	Remote Similarity	NPD2353	Approved
0.6629	Remote Similarity	NPD1471	Phase 3
0.6629	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD230	Phase 1
0.6627	Remote Similarity	NPD4908	Phase 1
0.6626	Remote Similarity	NPD1651	Approved
0.6617	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7783	Phase 2
0.6603	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7199	Phase 2
0.6587	Remote Similarity	NPD1283	Approved
0.6583	Remote Similarity	NPD3819	Phase 2
0.6582	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD454	Approved
0.6566	Remote Similarity	NPD4878	Approved
0.6554	Remote Similarity	NPD2654	Approved
0.655	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3365	Discontinued
0.6522	Remote Similarity	NPD958	Approved
0.6514	Remote Similarity	NPD5588	Approved
0.6514	Remote Similarity	NPD5960	Phase 3
0.6514	Remote Similarity	NPD7033	Discontinued
0.6506	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4534	Discontinued

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