NPASS Compound

Structure

NPC470562 OpenBabel07101718222D 30 32 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 6.0622 -1.5000 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 4.3301 -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 -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 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 6.0622 -0.5000 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 4 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 24 1 0 0 0 0 13 7 1 6 0 0 0 13 17 1 0 0 0 0 13 29 1 0 0 0 0 14 18 2 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.11
Volume:	419.05
LogP:	6.04
LogD:	3.028
LogS:	-3.265
# Rotatable Bonds:	6
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	3.307
Fsp3:	0.273
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:	-5.374
MDCK Permeability:	1.8448889022693038e-05
Pgp-inhibitor:	0.59
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.089
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.6541976928711%
Volume Distribution (VD):	0.513
Pgp-substrate:	6.280692100524902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.778
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.289
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.695
CYP2C9-substrate:	0.785
CYP2D6-inhibitor:	0.149
CYP2D6-substrate:	0.306
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	3.933
Half-life (T1/2):	0.473

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.452
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.817
Skin Sensitization:	0.931
Carcinogencity:	0.258
Eye Corrosion:	0.003
Eye Irritation:	0.883
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC470562

Natural Product ID:	NPC470562
*Common Name:**	(-)-(1's)-6,1'-O,O-Dimethyl-7-Chloroaverantin
IUPAC Name:	2-chloro-1,6,8-trihydroxy-3-methoxy-7-[(1S)-1-methoxyhexyl]anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	ZASRCJJQHPCHMP-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C22H23ClO7/c1-4-5-6-7-13(29-2)17-12(24)8-10-15(21(17)27)20(26)16-11(19(10)25)9-14(30-3)18(23)22(16)28/h8-9,13,24,27-28H,4-7H2,1-3H3/t13-/m0/s1
SMILES:	CCCCCC(C1=C(C=C2C(=C1O)C(=O)C3=C(C(=C(C=C3C2=O)OC)Cl)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071281
PubChem CID:	60199739
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	>	50000.0	nM	PMID[511961]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[511961]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[511961]

☑ 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 NPC470562 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	463
0.1-0.2	2042
0.2-0.3	5034
0.3-0.4	12476
0.4-0.5	5834
0.5-0.6	5606
0.6-0.7	6206
0.7-0.8	4775
0.8-0.85	189
0.85-0.9	57
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC470560
0.9752	High Similarity	NPC470565
0.9623	High Similarity	NPC470561
0.9563	High Similarity	NPC470563
0.9313	High Similarity	NPC470559
0.9273	High Similarity	NPC277865
0.9222	High Similarity	NPC264922
0.9217	High Similarity	NPC474857
0.9068	High Similarity	NPC470564
0.8966	High Similarity	NPC316091
0.8875	High Similarity	NPC470568
0.8857	High Similarity	NPC313386
0.8837	High Similarity	NPC306240
0.882	High Similarity	NPC470569
0.8721	High Similarity	NPC45072
0.8713	High Similarity	NPC470422
0.8688	High Similarity	NPC190648
0.8688	High Similarity	NPC312929
0.8688	High Similarity	NPC245584
0.8688	High Similarity	NPC289042
0.8688	High Similarity	NPC56433
0.8688	High Similarity	NPC118027
0.8688	High Similarity	NPC126767
0.8678	High Similarity	NPC151292
0.8667	High Similarity	NPC313541
0.865	High Similarity	NPC154683
0.865	High Similarity	NPC40356
0.8642	High Similarity	NPC147735
0.8642	High Similarity	NPC290954
0.8642	High Similarity	NPC255641
0.8636	High Similarity	NPC191606
0.858	High Similarity	NPC68850
0.8562	High Similarity	NPC34482
0.8554	High Similarity	NPC197326
0.8528	High Similarity	NPC294646
0.8509	High Similarity	NPC470570
0.85	High Similarity	NPC48762
0.85	High Similarity	NPC19896
0.8485	Intermediate Similarity	NPC208806
0.8483	Intermediate Similarity	NPC474499
0.848	Intermediate Similarity	NPC472032
0.8457	Intermediate Similarity	NPC34802
0.8447	Intermediate Similarity	NPC49282
0.8438	Intermediate Similarity	NPC167663
0.8434	Intermediate Similarity	NPC226656
0.8434	Intermediate Similarity	NPC66508
0.8393	Intermediate Similarity	NPC324736
0.8385	Intermediate Similarity	NPC21599
0.8385	Intermediate Similarity	NPC193703
0.8373	Intermediate Similarity	NPC107109
0.8364	Intermediate Similarity	NPC72958
0.8364	Intermediate Similarity	NPC149526
0.8364	Intermediate Similarity	NPC474417
0.8364	Intermediate Similarity	NPC232645
0.8364	Intermediate Similarity	NPC478148
0.8354	Intermediate Similarity	NPC329933
0.8333	Intermediate Similarity	NPC37543
0.8333	Intermediate Similarity	NPC199463
0.8323	Intermediate Similarity	NPC84266
0.8313	Intermediate Similarity	NPC87708
0.8293	Intermediate Similarity	NPC172329
0.8293	Intermediate Similarity	NPC2569
0.8274	Intermediate Similarity	NPC77807
0.8274	Intermediate Similarity	NPC14561
0.8274	Intermediate Similarity	NPC5379
0.8263	Intermediate Similarity	NPC93552
0.8263	Intermediate Similarity	NPC214632
0.8261	Intermediate Similarity	NPC49108
0.8261	Intermediate Similarity	NPC135524
0.8261	Intermediate Similarity	NPC94076
0.8261	Intermediate Similarity	NPC182255
0.8253	Intermediate Similarity	NPC46882
0.8253	Intermediate Similarity	NPC132990
0.8242	Intermediate Similarity	NPC65589
0.8242	Intermediate Similarity	NPC97029
0.8242	Intermediate Similarity	NPC97028
0.8242	Intermediate Similarity	NPC158338
0.8242	Intermediate Similarity	NPC100985
0.8242	Intermediate Similarity	NPC288036
0.8239	Intermediate Similarity	NPC477568
0.8235	Intermediate Similarity	NPC470342
0.8235	Intermediate Similarity	NPC472052
0.8235	Intermediate Similarity	NPC470810
0.8235	Intermediate Similarity	NPC472060
0.8225	Intermediate Similarity	NPC263483
0.8225	Intermediate Similarity	NPC178976
0.8225	Intermediate Similarity	NPC474637
0.8221	Intermediate Similarity	NPC28632
0.8221	Intermediate Similarity	NPC478019
0.8208	Intermediate Similarity	NPC477835
0.8204	Intermediate Similarity	NPC470338
0.8204	Intermediate Similarity	NPC470340
0.8204	Intermediate Similarity	NPC470337
0.8204	Intermediate Similarity	NPC268992
0.8204	Intermediate Similarity	NPC180944
0.8204	Intermediate Similarity	NPC51824
0.8204	Intermediate Similarity	NPC113608
0.8199	Intermediate Similarity	NPC253822
0.8199	Intermediate Similarity	NPC305845
0.8199	Intermediate Similarity	NPC204045
0.8198	Intermediate Similarity	NPC470081
0.8193	Intermediate Similarity	NPC202595
0.8193	Intermediate Similarity	NPC280295
0.8187	Intermediate Similarity	NPC298401
0.8182	Intermediate Similarity	NPC256672
0.8182	Intermediate Similarity	NPC27221
0.8182	Intermediate Similarity	NPC7025
0.8182	Intermediate Similarity	NPC472056
0.8172	Intermediate Similarity	NPC154720
0.8171	Intermediate Similarity	NPC163846
0.8171	Intermediate Similarity	NPC225173
0.8171	Intermediate Similarity	NPC474004
0.8167	Intermediate Similarity	NPC99937
0.8161	Intermediate Similarity	NPC470566
0.8161	Intermediate Similarity	NPC234497
0.8161	Intermediate Similarity	NPC470341
0.8161	Intermediate Similarity	NPC472058
0.8161	Intermediate Similarity	NPC324522
0.8161	Intermediate Similarity	NPC105414
0.816	Intermediate Similarity	NPC475201
0.8155	Intermediate Similarity	NPC155686
0.8155	Intermediate Similarity	NPC210942
0.8155	Intermediate Similarity	NPC329844
0.8155	Intermediate Similarity	NPC169990
0.815	Intermediate Similarity	NPC472051
0.815	Intermediate Similarity	NPC472057
0.8148	Intermediate Similarity	NPC268204
0.8148	Intermediate Similarity	NPC52789
0.8148	Intermediate Similarity	NPC26051
0.8148	Intermediate Similarity	NPC55832
0.8146	Intermediate Similarity	NPC471802
0.8144	Intermediate Similarity	NPC230848
0.814	Intermediate Similarity	NPC473696
0.814	Intermediate Similarity	NPC474096
0.8137	Intermediate Similarity	NPC472366
0.8133	Intermediate Similarity	NPC80370
0.8133	Intermediate Similarity	NPC10027
0.8133	Intermediate Similarity	NPC65775
0.8129	Intermediate Similarity	NPC284495
0.8129	Intermediate Similarity	NPC84571
0.8121	Intermediate Similarity	NPC22005
0.8121	Intermediate Similarity	NPC7943
0.8121	Intermediate Similarity	NPC123202
0.8121	Intermediate Similarity	NPC125801
0.8118	Intermediate Similarity	NPC201127
0.8114	Intermediate Similarity	NPC470567
0.811	Intermediate Similarity	NPC476055
0.8107	Intermediate Similarity	NPC68727
0.8098	Intermediate Similarity	NPC215451
0.8098	Intermediate Similarity	NPC277369
0.8098	Intermediate Similarity	NPC3732
0.8098	Intermediate Similarity	NPC221185
0.8092	Intermediate Similarity	NPC100849
0.8087	Intermediate Similarity	NPC470099
0.8086	Intermediate Similarity	NPC259166
0.8086	Intermediate Similarity	NPC80962
0.8086	Intermediate Similarity	NPC326109
0.8086	Intermediate Similarity	NPC48624
0.8086	Intermediate Similarity	NPC172250
0.8086	Intermediate Similarity	NPC144118
0.8086	Intermediate Similarity	NPC213659
0.8086	Intermediate Similarity	NPC215311
0.8086	Intermediate Similarity	NPC204985
0.8086	Intermediate Similarity	NPC219917
0.8086	Intermediate Similarity	NPC101366
0.8084	Intermediate Similarity	NPC474660
0.8084	Intermediate Similarity	NPC225854
0.8081	Intermediate Similarity	NPC311740
0.8075	Intermediate Similarity	NPC138099
0.8075	Intermediate Similarity	NPC1268
0.8075	Intermediate Similarity	NPC242994
0.807	Intermediate Similarity	NPC85121
0.8063	Intermediate Similarity	NPC471905
0.8061	Intermediate Similarity	NPC290133
0.8061	Intermediate Similarity	NPC187282
0.8061	Intermediate Similarity	NPC300540
0.8061	Intermediate Similarity	NPC469758
0.8061	Intermediate Similarity	NPC24136
0.8059	Intermediate Similarity	NPC180924
0.8059	Intermediate Similarity	NPC146211
0.8059	Intermediate Similarity	NPC280497
0.8059	Intermediate Similarity	NPC472050
0.8054	Intermediate Similarity	NPC247104
0.8054	Intermediate Similarity	NPC214901
0.8049	Intermediate Similarity	NPC475705
0.8049	Intermediate Similarity	NPC51887
0.8049	Intermediate Similarity	NPC117836
0.8049	Intermediate Similarity	NPC244691
0.8049	Intermediate Similarity	NPC471906
0.8049	Intermediate Similarity	NPC476178
0.8047	Intermediate Similarity	NPC135522
0.8046	Intermediate Similarity	NPC73544
0.8046	Intermediate Similarity	NPC316262
0.8046	Intermediate Similarity	NPC173352
0.8046	Intermediate Similarity	NPC314653
0.8046	Intermediate Similarity	NPC58653
0.8037	Intermediate Similarity	NPC40118
0.8037	Intermediate Similarity	NPC232021
0.8037	Intermediate Similarity	NPC474961
0.8037	Intermediate Similarity	NPC470087

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 NPC470562 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	1104
0.2-0.3	1908
0.3-0.4	2794
0.4-0.5	1749
0.5-0.6	863
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
0.8081	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6232	Discontinued
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7836	Intermediate Similarity	NPD7819	Suspended
0.7784	Intermediate Similarity	NPD2532	Approved
0.7784	Intermediate Similarity	NPD2534	Approved
0.7784	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7764	Intermediate Similarity	NPD1607	Approved
0.7733	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4380	Phase 2
0.764	Intermediate Similarity	NPD1240	Approved
0.764	Intermediate Similarity	NPD2403	Approved
0.7636	Intermediate Similarity	NPD1549	Phase 2
0.7576	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7515	Intermediate Similarity	NPD2796	Approved
0.7514	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD1934	Approved
0.7429	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD5844	Phase 1
0.7371	Intermediate Similarity	NPD6801	Discontinued
0.7348	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7768	Phase 2
0.7345	Intermediate Similarity	NPD3882	Suspended
0.733	Intermediate Similarity	NPD2801	Approved
0.733	Intermediate Similarity	NPD4360	Phase 2
0.733	Intermediate Similarity	NPD4363	Phase 3
0.7318	Intermediate Similarity	NPD5494	Approved
0.7316	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7303	Intermediate Similarity	NPD3749	Approved
0.7278	Intermediate Similarity	NPD2800	Approved
0.7257	Intermediate Similarity	NPD6599	Discontinued
0.7253	Intermediate Similarity	NPD6166	Phase 2
0.7253	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5710	Approved
0.7238	Intermediate Similarity	NPD5711	Approved
0.7235	Intermediate Similarity	NPD3750	Approved
0.7229	Intermediate Similarity	NPD6651	Approved
0.7209	Intermediate Similarity	NPD1511	Approved
0.7207	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1470	Approved
0.7204	Intermediate Similarity	NPD6559	Discontinued
0.7202	Intermediate Similarity	NPD4361	Phase 2
0.7202	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3818	Discontinued
0.716	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1512	Approved
0.711	Intermediate Similarity	NPD6799	Approved
0.7101	Intermediate Similarity	NPD6100	Approved
0.7101	Intermediate Similarity	NPD1551	Phase 2
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD6099	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5953	Discontinued
0.7056	Intermediate Similarity	NPD6778	Approved
0.7056	Intermediate Similarity	NPD6779	Approved
0.7056	Intermediate Similarity	NPD6781	Approved
0.7056	Intermediate Similarity	NPD6780	Approved
0.7056	Intermediate Similarity	NPD6782	Approved
0.7056	Intermediate Similarity	NPD6776	Approved
0.7056	Intermediate Similarity	NPD6777	Approved
0.7043	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8151	Discontinued
0.7011	Intermediate Similarity	NPD7041	Phase 2
0.7011	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD943	Approved
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7074	Phase 3
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6989	Remote Similarity	NPD920	Approved
0.6983	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD1201	Approved
0.6952	Remote Similarity	NPD7054	Approved
0.6952	Remote Similarity	NPD7286	Phase 2
0.695	Remote Similarity	NPD7698	Approved
0.695	Remote Similarity	NPD7697	Approved
0.695	Remote Similarity	NPD7696	Phase 3
0.695	Remote Similarity	NPD7435	Discontinued
0.6947	Remote Similarity	NPD8313	Approved
0.6947	Remote Similarity	NPD8312	Approved
0.6944	Remote Similarity	NPD1465	Phase 2
0.6941	Remote Similarity	NPD2799	Discontinued
0.6941	Remote Similarity	NPD3748	Approved
0.6936	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4628	Phase 3
0.6936	Remote Similarity	NPD7003	Approved
0.6915	Remote Similarity	NPD7472	Approved
0.6915	Remote Similarity	NPD7870	Phase 2
0.6915	Remote Similarity	NPD7871	Phase 2
0.691	Remote Similarity	NPD7458	Discontinued
0.6906	Remote Similarity	NPD5402	Approved
0.6897	Remote Similarity	NPD3887	Approved
0.6895	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6234	Discontinued
0.6879	Remote Similarity	NPD1243	Approved
0.6878	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6797	Phase 2
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD4965	Approved
0.6868	Remote Similarity	NPD4966	Approved
0.6868	Remote Similarity	NPD4967	Phase 2
0.6842	Remote Similarity	NPD7251	Discontinued
0.6839	Remote Similarity	NPD8150	Discontinued
0.6828	Remote Similarity	NPD3926	Phase 2
0.6826	Remote Similarity	NPD4625	Phase 3
0.6814	Remote Similarity	NPD7701	Phase 2
0.6813	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3751	Discontinued
0.6806	Remote Similarity	NPD7808	Phase 3
0.6806	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6535	Approved
0.6802	Remote Similarity	NPD6534	Approved
0.68	Remote Similarity	NPD2309	Approved
0.68	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2354	Approved
0.6798	Remote Similarity	NPD5403	Approved
0.6798	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.678	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7229	Phase 3
0.6761	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7874	Approved
0.6748	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2798	Approved
0.6744	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6823	Phase 2
0.672	Remote Similarity	NPD1247	Approved
0.672	Remote Similarity	NPD7177	Discontinued
0.6715	Remote Similarity	NPD7801	Approved
0.6707	Remote Similarity	NPD3972	Approved
0.6703	Remote Similarity	NPD919	Approved
0.67	Remote Similarity	NPD7700	Phase 2
0.67	Remote Similarity	NPD7699	Phase 2
0.6686	Remote Similarity	NPD2313	Discontinued
0.6686	Remote Similarity	NPD3764	Approved
0.6685	Remote Similarity	NPD5401	Approved
0.6685	Remote Similarity	NPD1578	Phase 2
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD2353	Approved
0.6648	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6273	Approved
0.6632	Remote Similarity	NPD7228	Approved
0.6632	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1283	Approved
0.6615	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD454	Approved
0.6606	Remote Similarity	NPD4878	Approved
0.6596	Remote Similarity	NPD3787	Discontinued
0.6591	Remote Similarity	NPD2654	Approved
0.659	Remote Similarity	NPD4538	Approved
0.659	Remote Similarity	NPD4536	Approved
0.659	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8319	Approved
0.6585	Remote Similarity	NPD8320	Phase 1
0.6583	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6213	Phase 3
0.6583	Remote Similarity	NPD6212	Phase 3
0.6582	Remote Similarity	NPD8434	Phase 2
0.6578	Remote Similarity	NPD3365	Discontinued
0.6576	Remote Similarity	NPD5760	Phase 2
0.6576	Remote Similarity	NPD5761	Phase 2
0.6567	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD958	Approved
0.6555	Remote Similarity	NPD7783	Phase 2
0.6555	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7199	Phase 2
0.6534	Remote Similarity	NPD4534	Discontinued
0.6533	Remote Similarity	NPD3819	Phase 2
0.6527	Remote Similarity	NPD1876	Approved
0.6526	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4626	Approved
0.6515	Remote Similarity	NPD4287	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