NPASS Compound

Structure

NPC34482 OpenBabel07101719242D 28 30 0 0 1 0 0 0 0 0999 V2000 -0.8660 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 1.7321 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 -4.3301 -0.5000 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 -4.3301 -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 -0.8660 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 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 0.0000 0.0000 0.0000 C 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 -3.4641 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 -1.7321 -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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 28 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 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 13 2 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 22 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 18 2 0 0 0 0 14 24 1 0 0 0 0 15 6 1 6 0 0 0 15 18 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 18 21 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 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	386.543
LogP:	5.31
LogD:	2.824
LogS:	-2.989
# Rotatable Bonds:	5
TPSA:	130.61
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	3.247
Fsp3:	0.238
Lipinski Rule-of-5:	Rejected
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:	-5.692
MDCK Permeability:	1.5725612684036605e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.552
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.14635467529297%
Volume Distribution (VD):	0.52
Pgp-substrate:	5.505050182342529%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.474
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.79
CYP2D6-inhibitor:	0.226
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.104
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	6.581
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.597
Drug-inuced Liver Injury (DILI):	0.665
AMES Toxicity:	0.585
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.949
Carcinogencity:	0.14
Eye Corrosion:	0.003
Eye Irritation:	0.896
Respiratory Toxicity:	0.256

Download Data

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

Natural Product: NPC34482

Natural Product ID:	NPC34482
*Common Name:**	(-)-1'-O-Methylaverantin
IUPAC Name:	1,3,6,8-tetrahydroxy-2-[(1S)-1-methoxyhexyl]anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	RNOYIZPXILLZCR-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C21H22O7/c1-3-4-5-6-15(28-2)18-14(24)9-12-17(21(18)27)20(26)16-11(19(12)25)7-10(22)8-13(16)23/h7-9,15,22-24,27H,3-6H2,1-2H3/t15-/m0/s1
SMILES:	CCCCC[C@@H](c1c(O)cc2c(c1O)C(=O)c1c(C2=O)cc(cc1O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071289
PubChem CID:	70684687
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
Others	2

Activity Type	# Activity
Cell Line	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	33590.0	nM	PMID[506462]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	35310.0	nM	PMID[506462]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	44220.0	nM	PMID[506462]
NPT35	Others	n.a.		Activity	<	50.0	%	PMID[506463]
NPT2	Others	Unspecified		Inhibition	=	10.0	%	PMID[506463]

☑ 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 NPC34482 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	365
0.1-0.2	1524
0.2-0.3	3432
0.3-0.4	8329
0.4-0.5	10492
0.5-0.6	3966
0.6-0.7	6177
0.7-0.8	5862
0.8-0.85	1857
0.85-0.9	606
0.9-0.95	77
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC48762
0.9928	High Similarity	NPC470570
0.9784	High Similarity	NPC21599
0.9784	High Similarity	NPC193703
0.965	High Similarity	NPC470568
0.964	High Similarity	NPC135524
0.9583	High Similarity	NPC470569
0.9568	High Similarity	NPC204045
0.9568	High Similarity	NPC305845
0.9441	High Similarity	NPC245584
0.9441	High Similarity	NPC289042
0.9441	High Similarity	NPC118027
0.9441	High Similarity	NPC190648
0.9441	High Similarity	NPC56433
0.9441	High Similarity	NPC312929
0.9441	High Similarity	NPC126767
0.9424	High Similarity	NPC242994
0.9424	High Similarity	NPC138099
0.942	High Similarity	NPC471905
0.9384	High Similarity	NPC154683
0.9384	High Similarity	NPC40356
0.9379	High Similarity	NPC290954
0.9379	High Similarity	NPC280295
0.9379	High Similarity	NPC255641
0.9379	High Similarity	NPC147735
0.9366	High Similarity	NPC471906
0.9366	High Similarity	NPC244691
0.9362	High Similarity	NPC474961
0.9357	High Similarity	NPC169452
0.9357	High Similarity	NPC181560
0.9348	High Similarity	NPC254847
0.9286	High Similarity	NPC190457
0.9281	High Similarity	NPC53206
0.9281	High Similarity	NPC53414
0.9247	High Similarity	NPC294646
0.9231	High Similarity	NPC19896
0.9225	High Similarity	NPC193555
0.9209	High Similarity	NPC191976
0.9189	High Similarity	NPC208806
0.9172	High Similarity	NPC34802
0.9167	High Similarity	NPC49282
0.9161	High Similarity	NPC167663
0.9155	High Similarity	NPC246638
0.9149	High Similarity	NPC143438
0.913	High Similarity	NPC267205
0.9128	High Similarity	NPC226656
0.9128	High Similarity	NPC66508
0.9116	High Similarity	NPC205766
0.9091	High Similarity	NPC73061
0.9073	High Similarity	NPC324736
0.9065	High Similarity	NPC282780
0.9065	High Similarity	NPC44437
0.9065	High Similarity	NPC166480
0.906	High Similarity	NPC107109
0.9054	High Similarity	NPC232645
0.9054	High Similarity	NPC474417
0.9054	High Similarity	NPC72958
0.9054	High Similarity	NPC149526
0.9054	High Similarity	NPC478148
0.9048	High Similarity	NPC329933
0.9034	High Similarity	NPC478019
0.9028	High Similarity	NPC159721
0.9028	High Similarity	NPC66593
0.9028	High Similarity	NPC84266
0.9007	High Similarity	NPC199463
0.9007	High Similarity	NPC37543
0.8993	High Similarity	NPC87708
0.898	High Similarity	NPC2569
0.898	High Similarity	NPC172329
0.8966	High Similarity	NPC151607
0.8966	High Similarity	NPC42540
0.8958	High Similarity	NPC182255
0.8958	High Similarity	NPC49108
0.8958	High Similarity	NPC94076
0.8951	High Similarity	NPC156872
0.894	High Similarity	NPC77807
0.894	High Similarity	NPC5379
0.894	High Similarity	NPC14561
0.8933	High Similarity	NPC214632
0.8933	High Similarity	NPC93552
0.8926	High Similarity	NPC46882
0.8926	High Similarity	NPC132990
0.8919	High Similarity	NPC158338
0.8919	High Similarity	NPC97028
0.8919	High Similarity	NPC100985
0.8919	High Similarity	NPC65589
0.8919	High Similarity	NPC288036
0.8919	High Similarity	NPC97029
0.8912	High Similarity	NPC37709
0.8897	High Similarity	NPC471731
0.8896	High Similarity	NPC470561
0.8889	High Similarity	NPC290550
0.8889	High Similarity	NPC472052
0.8889	High Similarity	NPC187843
0.8889	High Similarity	NPC472603
0.8889	High Similarity	NPC470810
0.8889	High Similarity	NPC470342
0.8889	High Similarity	NPC472060
0.8889	High Similarity	NPC253822
0.8882	High Similarity	NPC263483
0.8882	High Similarity	NPC178976
0.8874	High Similarity	NPC66029
0.8867	High Similarity	NPC470340
0.8867	High Similarity	NPC470338
0.8867	High Similarity	NPC268992
0.8867	High Similarity	NPC470337
0.8867	High Similarity	NPC51824
0.8867	High Similarity	NPC113608
0.8867	High Similarity	NPC180944
0.8859	High Similarity	NPC477914
0.8859	High Similarity	NPC202595
0.8851	High Similarity	NPC27221
0.8851	High Similarity	NPC472056
0.8851	High Similarity	NPC7025
0.8851	High Similarity	NPC256672
0.8846	High Similarity	NPC477835
0.8844	High Similarity	NPC300540
0.8844	High Similarity	NPC225173
0.8844	High Similarity	NPC163846
0.8844	High Similarity	NPC147250
0.8839	High Similarity	NPC470563
0.8836	High Similarity	NPC475201
0.8828	High Similarity	NPC471733
0.8828	High Similarity	NPC52789
0.8828	High Similarity	NPC268204
0.8828	High Similarity	NPC55832
0.8828	High Similarity	NPC137649
0.8828	High Similarity	NPC26051
0.8819	High Similarity	NPC472600
0.8819	High Similarity	NPC109232
0.8819	High Similarity	NPC472366
0.8819	High Similarity	NPC168471
0.8819	High Similarity	NPC472601
0.8811	High Similarity	NPC191835
0.8808	High Similarity	NPC329844
0.8808	High Similarity	NPC155686
0.8808	High Similarity	NPC169990
0.8808	High Similarity	NPC210942
0.8803	High Similarity	NPC118919
0.8803	High Similarity	NPC158481
0.88	High Similarity	NPC230848
0.8792	High Similarity	NPC80370
0.8792	High Similarity	NPC65775
0.8792	High Similarity	NPC477221
0.8792	High Similarity	NPC10027
0.879	High Similarity	NPC472058
0.879	High Similarity	NPC470341
0.879	High Similarity	NPC324522
0.879	High Similarity	NPC105414
0.879	High Similarity	NPC234497
0.8784	High Similarity	NPC125801
0.8784	High Similarity	NPC162751
0.8784	High Similarity	NPC290194
0.8784	High Similarity	NPC22005
0.8784	High Similarity	NPC123202
0.8784	High Similarity	NPC7943
0.8784	High Similarity	NPC52161
0.8784	High Similarity	NPC119767
0.8776	High Similarity	NPC28632
0.8776	High Similarity	NPC476055
0.8776	High Similarity	NPC474630
0.8767	High Similarity	NPC174905
0.8767	High Similarity	NPC474203
0.8767	High Similarity	NPC313047
0.8767	High Similarity	NPC295712
0.8767	High Similarity	NPC277369
0.8767	High Similarity	NPC215451
0.8767	High Similarity	NPC293545
0.8767	High Similarity	NPC451542
0.8767	High Similarity	NPC3732
0.8766	High Similarity	NPC84571
0.8766	High Similarity	NPC284495
0.8759	High Similarity	NPC259166
0.8759	High Similarity	NPC472604
0.8759	High Similarity	NPC101366
0.8759	High Similarity	NPC144118
0.8759	High Similarity	NPC80962
0.8759	High Similarity	NPC326109
0.8759	High Similarity	NPC204985
0.8759	High Similarity	NPC215311
0.8759	High Similarity	NPC172250
0.8759	High Similarity	NPC48624
0.8759	High Similarity	NPC219917
0.8759	High Similarity	NPC53649
0.8759	High Similarity	NPC472605
0.8759	High Similarity	NPC213659
0.8759	High Similarity	NPC110810
0.8758	High Similarity	NPC474637
0.8758	High Similarity	NPC201127
0.875	High Similarity	NPC19622
0.875	High Similarity	NPC112789
0.875	High Similarity	NPC162939
0.875	High Similarity	NPC68727
0.875	High Similarity	NPC1268
0.8742	High Similarity	NPC164912
0.8742	High Similarity	NPC149889
0.8742	High Similarity	NPC312338
0.8741	High Similarity	NPC194579
0.8741	High Similarity	NPC53001
0.8741	High Similarity	NPC70380

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 NPC34482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	977
0.2-0.3	1483
0.3-0.4	2643
0.4-0.5	2049
0.5-0.6	1119
0.6-0.7	372
0.7-0.8	159
0.8-0.85	21
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9348	High Similarity	NPD1509	Clinical (unspecified phase)
0.8707	High Similarity	NPD7390	Discontinued
0.859	High Similarity	NPD6959	Discontinued
0.8535	High Similarity	NPD6232	Discontinued
0.8491	Intermediate Similarity	NPD7473	Discontinued
0.8442	Intermediate Similarity	NPD7819	Suspended
0.8417	Intermediate Similarity	NPD1470	Approved
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.8403	Intermediate Similarity	NPD1607	Approved
0.84	Intermediate Similarity	NPD2532	Approved
0.84	Intermediate Similarity	NPD2534	Approved
0.84	Intermediate Similarity	NPD2533	Approved
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1240	Approved
0.8247	Intermediate Similarity	NPD4380	Phase 2
0.8243	Intermediate Similarity	NPD1549	Phase 2
0.8231	Intermediate Similarity	NPD5406	Approved
0.8231	Intermediate Similarity	NPD5405	Approved
0.8231	Intermediate Similarity	NPD5404	Approved
0.8231	Intermediate Similarity	NPD5408	Approved
0.8176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD943	Approved
0.8129	Intermediate Similarity	NPD1201	Approved
0.8121	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD2796	Approved
0.8077	Intermediate Similarity	NPD7411	Suspended
0.8065	Intermediate Similarity	NPD3226	Approved
0.805	Intermediate Similarity	NPD7075	Discontinued
0.8025	Intermediate Similarity	NPD1934	Approved
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5844	Phase 1
0.7922	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3882	Suspended
0.7875	Intermediate Similarity	NPD7768	Phase 2
0.7866	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2801	Approved
0.784	Intermediate Similarity	NPD5494	Approved
0.7826	Intermediate Similarity	NPD3749	Approved
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7803	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6801	Discontinued
0.7785	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6166	Phase 2
0.7758	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5711	Approved
0.7744	Intermediate Similarity	NPD5710	Approved
0.7742	Intermediate Similarity	NPD1511	Approved
0.7716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2800	Approved
0.7712	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6559	Discontinued
0.7674	Intermediate Similarity	NPD8150	Discontinued
0.7667	Intermediate Similarity	NPD6651	Approved
0.7665	Intermediate Similarity	NPD3818	Discontinued
0.7662	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1512	Approved
0.7635	Intermediate Similarity	NPD3764	Approved
0.7632	Intermediate Similarity	NPD1551	Phase 2
0.7632	Intermediate Similarity	NPD6100	Approved
0.7632	Intermediate Similarity	NPD6099	Approved
0.7628	Intermediate Similarity	NPD6799	Approved
0.7614	Intermediate Similarity	NPD6534	Approved
0.7614	Intermediate Similarity	NPD6535	Approved
0.761	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD230	Phase 1
0.7582	Intermediate Similarity	NPD2344	Approved
0.7571	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2799	Discontinued
0.7548	Intermediate Similarity	NPD7003	Approved
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7515	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7486	Intermediate Similarity	NPD7699	Phase 2
0.7486	Intermediate Similarity	NPD7700	Phase 2
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7471	Intermediate Similarity	NPD7074	Phase 3
0.7469	Intermediate Similarity	NPD37	Approved
0.7459	Intermediate Similarity	NPD8151	Discontinued
0.7451	Intermediate Similarity	NPD3748	Approved
0.7436	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7415	Intermediate Similarity	NPD1164	Approved
0.7412	Intermediate Similarity	NPD7054	Approved
0.7399	Intermediate Similarity	NPD8313	Approved
0.7399	Intermediate Similarity	NPD8312	Approved
0.7389	Intermediate Similarity	NPD2309	Approved
0.7378	Intermediate Similarity	NPD5402	Approved
0.7377	Intermediate Similarity	NPD7435	Discontinued
0.7377	Intermediate Similarity	NPD7697	Approved
0.7377	Intermediate Similarity	NPD7698	Approved
0.7377	Intermediate Similarity	NPD7696	Phase 3
0.7375	Intermediate Similarity	NPD920	Approved
0.7372	Intermediate Similarity	NPD1243	Approved
0.7368	Intermediate Similarity	NPD7472	Approved
0.7365	Intermediate Similarity	NPD2798	Approved
0.736	Intermediate Similarity	NPD6213	Phase 3
0.736	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6212	Phase 3
0.7349	Intermediate Similarity	NPD6234	Discontinued
0.7341	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7870	Phase 2
0.7337	Intermediate Similarity	NPD7871	Phase 2
0.7337	Intermediate Similarity	NPD8320	Phase 1
0.7337	Intermediate Similarity	NPD8319	Approved
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD4966	Approved
0.7329	Intermediate Similarity	NPD3972	Approved
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6797	Phase 2
0.7324	Intermediate Similarity	NPD9493	Approved
0.7317	Intermediate Similarity	NPD1465	Phase 2
0.731	Intermediate Similarity	NPD7286	Phase 2
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1651	Approved
0.7292	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2313	Discontinued
0.7283	Intermediate Similarity	NPD7251	Discontinued
0.7278	Intermediate Similarity	NPD3926	Phase 2
0.7267	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.725	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1471	Phase 3
0.7241	Intermediate Similarity	NPD3019	Approved
0.7241	Intermediate Similarity	NPD7808	Phase 3
0.7241	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1283	Approved
0.7222	Intermediate Similarity	NPD9545	Approved
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD7701	Phase 2
0.7209	Intermediate Similarity	NPD6020	Phase 2
0.7205	Intermediate Similarity	NPD6273	Approved
0.7204	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6190	Approved
0.716	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7151	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7874	Approved
0.7135	Intermediate Similarity	NPD6823	Phase 2
0.7125	Intermediate Similarity	NPD3300	Phase 2
0.7123	Intermediate Similarity	NPD4626	Approved
0.7123	Intermediate Similarity	NPD2932	Approved
0.7115	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1876	Approved
0.7107	Intermediate Similarity	NPD8166	Discontinued
0.7105	Intermediate Similarity	NPD7008	Discontinued
0.7105	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7801	Approved
0.7095	Intermediate Similarity	NPD9269	Phase 2
0.7071	Intermediate Similarity	NPD4750	Phase 3
0.7067	Intermediate Similarity	NPD1203	Approved
0.7055	Intermediate Similarity	NPD9268	Approved
0.7052	Intermediate Similarity	NPD7228	Approved
0.7052	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2654	Approved
0.7039	Intermediate Similarity	NPD6832	Phase 2
0.7033	Intermediate Similarity	NPD4360	Phase 2
0.7033	Intermediate Similarity	NPD4363	Phase 3
0.7027	Intermediate Similarity	NPD1281	Approved
0.7022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3787	Discontinued
0.7013	Intermediate Similarity	NPD6663	Approved
0.7007	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD5760	Phase 2
0.7006	Intermediate Similarity	NPD4308	Phase 3
0.6983	Remote Similarity	NPD8434	Phase 2
0.6974	Remote Similarity	NPD5736	Approved
0.6968	Remote Similarity	NPD2979	Phase 3
0.6962	Remote Similarity	NPD2438	Suspended
0.6959	Remote Similarity	NPD7199	Phase 2

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