NPASS Compound

Structure

CID21599 OpenBabel06191715342D 22 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 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 3.4641 0.0000 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 -0.0000 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 2.5981 0.5000 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 -0.8660 0.5000 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 -0.8660 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 -1.0000 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 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 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 10 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 22 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	291.273
LogP:	2.771
LogD:	1.764
LogS:	-3.104
# Rotatable Bonds:	1
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	3.122
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.942
MDCK Permeability:	1.562050420034211e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	96.61669158935547%
Volume Distribution (VD):	0.815
Pgp-substrate:	5.777862071990967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.632
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.72
CYP2C9-substrate:	0.611
CYP2D6-inhibitor:	0.677
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.417
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	6.069
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.574
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.847
Rat Oral Acute Toxicity:	0.592
Maximum Recommended Daily Dose:	0.258
Skin Sensitization:	0.488
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.197
Respiratory Toxicity:	0.839

Download Data

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

Natural Product: NPC21599

Natural Product ID:	NPC21599
*Common Name:**	1,3,5-Trihydroxy-2-(Methoxymethyl)Anthracene-9,10-Dione
IUPAC Name:	1,3,5-trihydroxy-2-(methoxymethyl)anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	QPAINZVYGPYFIU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O6/c1-22-6-9-11(18)5-8-13(16(9)21)14(19)7-3-2-4-10(17)12(7)15(8)20/h2-5,17-18,21H,6H2,1H3
SMILES:	COCc1c(O)cc2c(c1O)C(=O)c1c(C2=O)c(O)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452675
PubChem CID:	44575883
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
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15917	Monilinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26859	Solanum curtipes	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2868	Perna viridis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO861	Siphonaria funiculata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13446	Stachys recta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11734	Chara corallina	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[503809]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[503809]
NPT2	Others	Unspecified		Inhibition	=	51.8	%	PMID[503809]
NPT2	Others	Unspecified		Inhibition	=	21.0	%	PMID[503809]
NPT2	Others	Unspecified		Inhibition	=	5.7	%	PMID[503809]

☑ 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 NPC21599 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	370
0.1-0.2	1606
0.2-0.3	3607
0.3-0.4	9255
0.4-0.5	9425
0.5-0.6	3913
0.6-0.7	6235
0.7-0.8	5684
0.8-0.85	1910
0.85-0.9	608
0.9-0.95	75
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193703
0.9855	High Similarity	NPC48762
0.9784	High Similarity	NPC34482
0.9714	High Similarity	NPC470570
0.958	High Similarity	NPC255641
0.958	High Similarity	NPC290954
0.9507	High Similarity	NPC312929
0.9507	High Similarity	NPC118027
0.9507	High Similarity	NPC56433
0.9507	High Similarity	NPC245584
0.9507	High Similarity	NPC126767
0.9507	High Similarity	NPC289042
0.9507	High Similarity	NPC190648
0.9496	High Similarity	NPC305845
0.9496	High Similarity	NPC204045
0.9493	High Similarity	NPC242994
0.9493	High Similarity	NPC138099
0.9489	High Similarity	NPC471905
0.9489	High Similarity	NPC53414
0.9489	High Similarity	NPC53206
0.9444	High Similarity	NPC470568
0.9444	High Similarity	NPC147735
0.9429	High Similarity	NPC135524
0.9424	High Similarity	NPC169452
0.9424	High Similarity	NPC181560
0.9416	High Similarity	NPC254847
0.9384	High Similarity	NPC208806
0.9379	High Similarity	NPC470569
0.9353	High Similarity	NPC190457
0.9315	High Similarity	NPC154683
0.9315	High Similarity	NPC40356
0.931	High Similarity	NPC280295
0.931	High Similarity	NPC294646
0.9296	High Similarity	NPC19896
0.9296	High Similarity	NPC244691
0.9296	High Similarity	NPC471906
0.9291	High Similarity	NPC73061
0.9291	High Similarity	NPC193555
0.927	High Similarity	NPC44437
0.9231	High Similarity	NPC49282
0.9225	High Similarity	NPC66593
0.922	High Similarity	NPC246638
0.9214	High Similarity	NPC143438
0.9197	High Similarity	NPC267205
0.9189	High Similarity	NPC226656
0.9189	High Similarity	NPC66508
0.9178	High Similarity	NPC205766
0.9155	High Similarity	NPC474961
0.9137	High Similarity	NPC191976
0.9133	High Similarity	NPC324736
0.913	High Similarity	NPC166480
0.913	High Similarity	NPC282780
0.9122	High Similarity	NPC107109
0.911	High Similarity	NPC329933
0.9103	High Similarity	NPC34802
0.9097	High Similarity	NPC478019
0.9091	High Similarity	NPC167663
0.9067	High Similarity	NPC178976
0.9034	High Similarity	NPC300540
0.9028	High Similarity	NPC475201
0.9021	High Similarity	NPC182255
0.9021	High Similarity	NPC49108
0.9021	High Similarity	NPC94076
0.9014	High Similarity	NPC156872
0.9	High Similarity	NPC5379
0.9	High Similarity	NPC77807
0.9	High Similarity	NPC14561
0.8993	High Similarity	NPC214632
0.8986	High Similarity	NPC149526
0.8986	High Similarity	NPC230848
0.8986	High Similarity	NPC474417
0.8986	High Similarity	NPC478148
0.898	High Similarity	NPC80370
0.8973	High Similarity	NPC119767
0.8958	High Similarity	NPC84266
0.8951	High Similarity	NPC187843
0.8951	High Similarity	NPC101366
0.8951	High Similarity	NPC290550
0.8944	High Similarity	NPC1268
0.894	High Similarity	NPC199463
0.894	High Similarity	NPC37543
0.8933	High Similarity	NPC66029
0.8926	High Similarity	NPC149889
0.8926	High Similarity	NPC312338
0.8921	High Similarity	NPC52407
0.8919	High Similarity	NPC202595
0.8913	High Similarity	NPC93015
0.8912	High Similarity	NPC7025
0.8912	High Similarity	NPC2569
0.8912	High Similarity	NPC27221
0.8912	High Similarity	NPC472056
0.8912	High Similarity	NPC256672
0.8912	High Similarity	NPC172329
0.8905	High Similarity	NPC99731
0.8904	High Similarity	NPC147250
0.8904	High Similarity	NPC163846
0.8904	High Similarity	NPC225173
0.8897	High Similarity	NPC42540
0.8897	High Similarity	NPC151607
0.8889	High Similarity	NPC26051
0.8889	High Similarity	NPC311740
0.8889	High Similarity	NPC268204
0.8889	High Similarity	NPC55832
0.8889	High Similarity	NPC52789
0.8881	High Similarity	NPC109232
0.8881	High Similarity	NPC203063
0.8881	High Similarity	NPC295384
0.8881	High Similarity	NPC472366
0.8873	High Similarity	NPC4214
0.8873	High Similarity	NPC13715
0.8867	High Similarity	NPC169990
0.8867	High Similarity	NPC329844
0.8867	High Similarity	NPC210942
0.8867	High Similarity	NPC93552
0.8865	High Similarity	NPC158481
0.8865	High Similarity	NPC118919
0.8859	High Similarity	NPC258249
0.8859	High Similarity	NPC72958
0.8859	High Similarity	NPC232645
0.8859	High Similarity	NPC118427
0.8851	High Similarity	NPC100985
0.8851	High Similarity	NPC10027
0.8851	High Similarity	NPC158338
0.8851	High Similarity	NPC97028
0.8851	High Similarity	NPC65775
0.8851	High Similarity	NPC65589
0.8851	High Similarity	NPC288036
0.8851	High Similarity	NPC97029
0.8849	High Similarity	NPC70622
0.8844	High Similarity	NPC22005
0.8844	High Similarity	NPC123202
0.8844	High Similarity	NPC7943
0.8844	High Similarity	NPC125801
0.8844	High Similarity	NPC37709
0.8841	High Similarity	NPC31799
0.8836	High Similarity	NPC476055
0.8836	High Similarity	NPC28632
0.8832	High Similarity	NPC282923
0.8828	High Similarity	NPC451542
0.8828	High Similarity	NPC295712
0.8828	High Similarity	NPC474203
0.8828	High Similarity	NPC313047
0.8828	High Similarity	NPC159721
0.8824	High Similarity	NPC472060
0.8824	High Similarity	NPC84571
0.8824	High Similarity	NPC472052
0.8824	High Similarity	NPC470342
0.8819	High Similarity	NPC172250
0.8819	High Similarity	NPC110810
0.8819	High Similarity	NPC144118
0.8819	High Similarity	NPC253822
0.8819	High Similarity	NPC124365
0.8819	High Similarity	NPC215311
0.8819	High Similarity	NPC80962
0.8819	High Similarity	NPC213659
0.8819	High Similarity	NPC48624
0.8819	High Similarity	NPC326109
0.8819	High Similarity	NPC219917
0.8819	High Similarity	NPC204985
0.8819	High Similarity	NPC259166
0.8816	High Similarity	NPC263483
0.8811	High Similarity	NPC12175
0.8811	High Similarity	NPC19622
0.8811	High Similarity	NPC90665
0.8811	High Similarity	NPC279668
0.8811	High Similarity	NPC162939
0.8811	High Similarity	NPC26924
0.8811	High Similarity	NPC112789
0.8811	High Similarity	NPC55162
0.8811	High Similarity	NPC278323
0.8811	High Similarity	NPC309154
0.88	High Similarity	NPC164912
0.88	High Similarity	NPC87708
0.8794	High Similarity	NPC283088
0.8794	High Similarity	NPC161632
0.8774	High Similarity	NPC101769
0.8768	High Similarity	NPC92624
0.8759	High Similarity	NPC126534
0.8759	High Similarity	NPC69755
0.8759	High Similarity	NPC137649
0.8759	High Similarity	NPC232021
0.8759	High Similarity	NPC40118
0.8759	High Similarity	NPC469404
0.875	High Similarity	NPC183345
0.875	High Similarity	NPC99441
0.875	High Similarity	NPC477956
0.875	High Similarity	NPC155205
0.875	High Similarity	NPC168471
0.875	High Similarity	NPC315578
0.875	High Similarity	NPC275903
0.875	High Similarity	NPC283429
0.8742	High Similarity	NPC135522
0.8741	High Similarity	NPC209560
0.8741	High Similarity	NPC294409
0.8741	High Similarity	NPC416
0.8741	High Similarity	NPC116632
0.8741	High Similarity	NPC181124
0.8741	High Similarity	NPC7013
0.8741	High Similarity	NPC472419
0.8741	High Similarity	NPC303644

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 NPC21599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	989
0.2-0.3	1423
0.3-0.4	2662
0.4-0.5	2037
0.5-0.6	1142
0.6-0.7	375
0.7-0.8	157
0.8-0.85	22
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9416	High Similarity	NPD1509	Clinical (unspecified phase)
0.8639	High Similarity	NPD7390	Discontinued
0.8613	High Similarity	NPD1470	Approved
0.8601	High Similarity	NPD1510	Phase 2
0.8592	High Similarity	NPD1607	Approved
0.859	High Similarity	NPD6232	Discontinued
0.8544	High Similarity	NPD7473	Discontinued
0.8497	Intermediate Similarity	NPD7819	Suspended
0.8451	Intermediate Similarity	NPD1240	Approved
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD943	Approved
0.8321	Intermediate Similarity	NPD1201	Approved
0.8299	Intermediate Similarity	NPD1549	Phase 2
0.8288	Intermediate Similarity	NPD5406	Approved
0.8288	Intermediate Similarity	NPD5404	Approved
0.8288	Intermediate Similarity	NPD5408	Approved
0.8288	Intermediate Similarity	NPD5405	Approved
0.8258	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3226	Approved
0.8231	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4380	Phase 2
0.8176	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7411	Suspended
0.8077	Intermediate Similarity	NPD1934	Approved
0.8041	Intermediate Similarity	NPD2935	Discontinued
0.8041	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD3749	Approved
0.7987	Intermediate Similarity	NPD2346	Discontinued
0.7973	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3750	Approved
0.7925	Intermediate Similarity	NPD7768	Phase 2
0.7925	Intermediate Similarity	NPD3882	Suspended
0.7914	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2801	Approved
0.7908	Intermediate Similarity	NPD1511	Approved
0.7879	Intermediate Similarity	NPD5844	Phase 1
0.7857	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6599	Discontinued
0.7829	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3764	Approved
0.7806	Intermediate Similarity	NPD1512	Approved
0.78	Intermediate Similarity	NPD1551	Phase 2
0.7778	Intermediate Similarity	NPD5494	Approved
0.7763	Intermediate Similarity	NPD2800	Approved
0.7763	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2344	Approved
0.7746	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6801	Discontinued
0.7697	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6166	Phase 2
0.7697	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD5711	Approved
0.7683	Intermediate Similarity	NPD5710	Approved
0.7677	Intermediate Similarity	NPD6799	Approved
0.7654	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD230	Phase 1
0.7633	Intermediate Similarity	NPD6559	Discontinued
0.7616	Intermediate Similarity	NPD2799	Discontinued
0.7616	Intermediate Similarity	NPD8150	Discontinued
0.7616	Intermediate Similarity	NPD3748	Approved
0.7605	Intermediate Similarity	NPD3818	Discontinued
0.76	Intermediate Similarity	NPD6651	Approved
0.7597	Intermediate Similarity	NPD7003	Approved
0.7593	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1164	Approved
0.7574	Intermediate Similarity	NPD5953	Discontinued
0.7566	Intermediate Similarity	NPD6099	Approved
0.7566	Intermediate Similarity	NPD6100	Approved
0.7557	Intermediate Similarity	NPD6535	Approved
0.7557	Intermediate Similarity	NPD6534	Approved
0.7548	Intermediate Similarity	NPD2309	Approved
0.7547	Intermediate Similarity	NPD7458	Discontinued
0.7547	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD920	Approved
0.7531	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD9493	Approved
0.7456	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2313	Discontinued
0.7444	Intermediate Similarity	NPD6780	Approved
0.7444	Intermediate Similarity	NPD6778	Approved
0.7444	Intermediate Similarity	NPD6776	Approved
0.7444	Intermediate Similarity	NPD6782	Approved
0.7444	Intermediate Similarity	NPD6777	Approved
0.7444	Intermediate Similarity	NPD6781	Approved
0.7444	Intermediate Similarity	NPD6779	Approved
0.743	Intermediate Similarity	NPD7700	Phase 2
0.743	Intermediate Similarity	NPD7699	Phase 2
0.7429	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1243	Approved
0.7415	Intermediate Similarity	NPD2798	Approved
0.7412	Intermediate Similarity	NPD7074	Phase 3
0.7405	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.7397	Intermediate Similarity	NPD1283	Approved
0.7394	Intermediate Similarity	NPD9545	Approved
0.7389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD3972	Approved
0.7372	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7362	Intermediate Similarity	NPD1465	Phase 2
0.7353	Intermediate Similarity	NPD7286	Phase 2
0.7353	Intermediate Similarity	NPD7054	Approved
0.7348	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1651	Approved
0.7341	Intermediate Similarity	NPD8313	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7696	Phase 3
0.7322	Intermediate Similarity	NPD7698	Approved
0.7322	Intermediate Similarity	NPD7435	Discontinued
0.7322	Intermediate Similarity	NPD7697	Approved
0.7321	Intermediate Similarity	NPD3926	Phase 2
0.7317	Intermediate Similarity	NPD5402	Approved
0.7312	Intermediate Similarity	NPD8151	Discontinued
0.7312	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7472	Approved
0.7305	Intermediate Similarity	NPD1247	Approved
0.7303	Intermediate Similarity	NPD6213	Phase 3
0.7303	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6212	Phase 3
0.7301	Intermediate Similarity	NPD37	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7292	Intermediate Similarity	NPD3019	Approved
0.7289	Intermediate Similarity	NPD919	Approved
0.7283	Intermediate Similarity	NPD7870	Phase 2
0.7283	Intermediate Similarity	NPD7871	Phase 2
0.7283	Intermediate Similarity	NPD8319	Approved
0.7283	Intermediate Similarity	NPD8320	Phase 1
0.7279	Intermediate Similarity	NPD1876	Approved
0.7267	Intermediate Similarity	NPD6797	Phase 2
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.7251	Intermediate Similarity	NPD6020	Phase 2
0.723	Intermediate Similarity	NPD1203	Approved
0.7225	Intermediate Similarity	NPD7251	Discontinued
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5403	Approved
0.7204	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4908	Phase 1
0.7193	Intermediate Similarity	NPD7177	Discontinued
0.7192	Intermediate Similarity	NPD1281	Approved
0.7192	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5401	Approved
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6234	Discontinued
0.7184	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7808	Phase 3
0.7172	Intermediate Similarity	NPD4626	Approved
0.7172	Intermediate Similarity	NPD2932	Approved
0.717	Intermediate Similarity	NPD3300	Phase 2
0.7169	Intermediate Similarity	NPD4965	Approved
0.7169	Intermediate Similarity	NPD4966	Approved
0.7169	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7701	Phase 2
0.7161	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD6273	Approved
0.7107	Intermediate Similarity	NPD6190	Approved
0.7105	Intermediate Similarity	NPD411	Approved
0.7103	Intermediate Similarity	NPD9268	Approved
0.709	Intermediate Similarity	NPD7874	Approved
0.709	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD6823	Phase 2
0.7078	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1610	Phase 2
0.707	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7801	Approved
0.7039	Intermediate Similarity	NPD4287	Approved
0.7039	Intermediate Similarity	NPD7008	Discontinued
0.7027	Intermediate Similarity	NPD9717	Approved
0.702	Intermediate Similarity	NPD9494	Approved
0.7013	Intermediate Similarity	NPD2979	Phase 3
0.7006	Intermediate Similarity	NPD2296	Approved
0.7006	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD4750	Phase 3
0.7	Intermediate Similarity	NPD7199	Phase 2
0.6994	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD5951	Approved
0.6986	Remote Similarity	NPD5691	Approved
0.6981	Remote Similarity	NPD2654	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