NPASS Compound

Structure

NPC161964 OpenBabel07101719522D 36 41 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 1.7321 -3.0000 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 2.5981 -4.5000 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 3.4641 -0.0000 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 5.1962 -0.0000 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 4.3301 0.5000 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 2.5981 -2.5000 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 3.4641 -1.0000 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 3.4641 -4.0000 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 5.1962 -1.0000 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 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 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 0.8660 0.5000 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 -0.0000 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 19 2 0 0 0 0 8 20 2 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 15 25 2 0 0 0 0 16 26 2 0 0 0 0 17 23 1 0 0 0 0 17 27 2 0 0 0 0 18 24 1 0 0 0 0 18 28 2 0 0 0 0 19 25 1 0 0 0 0 19 31 1 0 0 0 0 20 26 1 0 0 0 0 20 32 1 0 0 0 0 21 27 1 0 0 0 0 21 33 1 0 0 0 0 22 28 1 0 0 0 0 22 34 1 0 0 0 0 23 15 1 1 0 0 0 23 24 1 0 0 0 0 24 16 1 1 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 29 35 2 0 0 0 0 30 36 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.14
Volume:	491.928
LogP:	7.444
LogD:	3.316
LogS:	-4.616
# Rotatable Bonds:	1
TPSA:	121.38
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	2.787
Fsp3:	0.067
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:	-5.791
MDCK Permeability:	8.358524610230234e-06
Pgp-inhibitor:	0.224
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.39
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	95.2079086303711%
Volume Distribution (VD):	0.276
Pgp-substrate:	6.926463603973389%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.201
CYP2C19-inhibitor:	0.517
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.671
CYP2C9-substrate:	0.835
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.464
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	4.198
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.025
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.608
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.962
Carcinogencity:	0.348
Eye Corrosion:	0.004
Eye Irritation:	0.955
Respiratory Toxicity:	0.209

Download Data

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

Natural Product: NPC161964

Natural Product ID:	NPC161964
*Common Name:**	(9R,9'r)-4,4',5,5'-Tetrahydroxy-2,2'-Dimethyl-9,9'-Bianthracene-10,10'(9H,9'h)-Dione
IUPAC Name:	(10R)-10-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-1,8-dihydroxy-3-methyl-10H-anthracen-9-one
Synonyms:
Standard InCHIKey:	IXXWTERKUADIKZ-DNQXCXABSA-N
Standard InCHI:	InChI=1S/C30H22O6/c1-13-9-17-23(15-5-3-7-19(31)25(15)29(35)27(17)21(33)11-13)24-16-6-4-8-20(32)26(16)30(36)28-18(24)10-14(2)12-22(28)34/h3-12,23-24,31-34H,1-2H3/t23-,24-/m1/s1
SMILES:	Cc1cc(O)c2c(c1)[C@H]([C@@H]1c3cccc(c3C(=O)c3c1cc(C)cc3O)O)c1c(C2=O)c(O)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517019
PubChem CID:	44567179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO32935	rhamnus nepalensis	Species	Rhamnaceae	Eukaryota	Leaves	Pa Co, Mai Chau, Hoa Binh Province, 150 km west of Hanoi, Vietnam	1995-Nov	PMID[11575949]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1200.0	nM	PMID[569156]

☑ 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 NPC161964 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	364
0.1-0.2	1632
0.2-0.3	3480
0.3-0.4	10010
0.4-0.5	9378
0.5-0.6	5976
0.6-0.7	8428
0.7-0.8	3078
0.8-0.85	252
0.85-0.9	69
0.9-0.95	27
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC287604
1.0	High Similarity	NPC472262
0.9403	High Similarity	NPC225243
0.9338	High Similarity	NPC451542
0.9338	High Similarity	NPC474203
0.9338	High Similarity	NPC295712
0.9338	High Similarity	NPC313047
0.9308	High Similarity	NPC474517
0.9308	High Similarity	NPC72669
0.9265	High Similarity	NPC19631
0.9265	High Similarity	NPC239136
0.9213	High Similarity	NPC173978
0.9197	High Similarity	NPC174905
0.9197	High Similarity	NPC293545
0.9197	High Similarity	NPC471682
0.9197	High Similarity	NPC296752
0.9179	High Similarity	NPC245923
0.9167	High Similarity	NPC115458
0.9124	High Similarity	NPC257644
0.9104	High Similarity	NPC474813
0.9091	High Similarity	NPC58685
0.9077	High Similarity	NPC48248
0.9077	High Similarity	NPC282923
0.9065	High Similarity	NPC471683
0.903	High Similarity	NPC283088
0.9023	High Similarity	NPC225051
0.8993	High Similarity	NPC227841
0.8963	High Similarity	NPC272268
0.8897	High Similarity	NPC62272
0.8872	High Similarity	NPC205992
0.8864	High Similarity	NPC146647
0.8864	High Similarity	NPC34414
0.8864	High Similarity	NPC99731
0.8857	High Similarity	NPC10764
0.8846	High Similarity	NPC103540
0.8832	High Similarity	NPC13715
0.8824	High Similarity	NPC155211
0.8811	High Similarity	NPC477221
0.8803	High Similarity	NPC37709
0.8803	High Similarity	NPC290194
0.8794	High Similarity	NPC12402
0.8779	High Similarity	NPC3224
0.8769	High Similarity	NPC142956
0.875	High Similarity	NPC80035
0.8732	High Similarity	NPC110882
0.8732	High Similarity	NPC271944
0.8732	High Similarity	NPC85393
0.8714	High Similarity	NPC85310
0.8705	High Similarity	NPC169452
0.8705	High Similarity	NPC181560
0.8705	High Similarity	NPC96421
0.8692	High Similarity	NPC375356
0.8686	High Similarity	NPC191976
0.8676	High Similarity	NPC12070
0.8667	High Similarity	NPC70622
0.8657	High Similarity	NPC55949
0.8643	High Similarity	NPC106519
0.8643	High Similarity	NPC91019
0.8643	High Similarity	NPC246638
0.8643	High Similarity	NPC477275
0.8633	High Similarity	NPC242994
0.8633	High Similarity	NPC138099
0.8623	High Similarity	NPC305060
0.8615	High Similarity	NPC300274
0.8613	High Similarity	NPC249272
0.8603	High Similarity	NPC267205
0.8603	High Similarity	NPC314048
0.8603	High Similarity	NPC53896
0.8603	High Similarity	NPC114183
0.8593	High Similarity	NPC244699
0.8582	High Similarity	NPC193555
0.8582	High Similarity	NPC276238
0.8571	High Similarity	NPC315578
0.854	High Similarity	NPC270899
0.854	High Similarity	NPC288089
0.854	High Similarity	NPC50924
0.8531	High Similarity	NPC68441
0.8531	High Similarity	NPC170055
0.8519	High Similarity	NPC199253
0.8519	High Similarity	NPC136588
0.8507	High Similarity	NPC96024
0.8504	High Similarity	NPC477453
0.8503	High Similarity	NPC474533
0.8503	High Similarity	NPC474534
0.85	High Similarity	NPC26924
0.85	High Similarity	NPC1268
0.8496	Intermediate Similarity	NPC160499
0.8496	Intermediate Similarity	NPC96915
0.8489	Intermediate Similarity	NPC471905
0.8489	Intermediate Similarity	NPC53206
0.8489	Intermediate Similarity	NPC53414
0.8489	Intermediate Similarity	NPC53001
0.8485	Intermediate Similarity	NPC199273
0.8473	Intermediate Similarity	NPC307174
0.8472	Intermediate Similarity	NPC147250
0.8462	Intermediate Similarity	NPC300684
0.8462	Intermediate Similarity	NPC48130
0.8462	Intermediate Similarity	NPC218866
0.8462	Intermediate Similarity	NPC477913
0.8462	Intermediate Similarity	NPC84568
0.8456	Intermediate Similarity	NPC41847
0.8456	Intermediate Similarity	NPC85342
0.8451	Intermediate Similarity	NPC469520
0.8451	Intermediate Similarity	NPC69755
0.8444	Intermediate Similarity	NPC109123
0.8435	Intermediate Similarity	NPC35
0.8433	Intermediate Similarity	NPC176130
0.8433	Intermediate Similarity	NPC78364
0.8433	Intermediate Similarity	NPC471530
0.8433	Intermediate Similarity	NPC69424
0.8433	Intermediate Similarity	NPC84672
0.8429	Intermediate Similarity	NPC87723
0.8429	Intermediate Similarity	NPC61398
0.8429	Intermediate Similarity	NPC416
0.8417	Intermediate Similarity	NPC193358
0.8417	Intermediate Similarity	NPC118919
0.8417	Intermediate Similarity	NPC254847
0.8417	Intermediate Similarity	NPC472308
0.8414	Intermediate Similarity	NPC215593
0.8414	Intermediate Similarity	NPC52161
0.8414	Intermediate Similarity	NPC162751
0.8406	Intermediate Similarity	NPC166480
0.8406	Intermediate Similarity	NPC282780
0.8394	Intermediate Similarity	NPC175738
0.8389	Intermediate Similarity	NPC266469
0.8382	Intermediate Similarity	NPC31799
0.838	Intermediate Similarity	NPC124365
0.8367	Intermediate Similarity	NPC205766
0.8367	Intermediate Similarity	NPC315520
0.8358	Intermediate Similarity	NPC231774
0.8358	Intermediate Similarity	NPC306765
0.8357	Intermediate Similarity	NPC474110
0.8357	Intermediate Similarity	NPC44960
0.8356	Intermediate Similarity	NPC106524
0.8356	Intermediate Similarity	NPC290695
0.8346	Intermediate Similarity	NPC234890
0.8346	Intermediate Similarity	NPC74507
0.8346	Intermediate Similarity	NPC68756
0.8346	Intermediate Similarity	NPC152525
0.8345	Intermediate Similarity	NPC285122
0.8345	Intermediate Similarity	NPC161632
0.8345	Intermediate Similarity	NPC472134
0.8333	Intermediate Similarity	NPC176208
0.8333	Intermediate Similarity	NPC52407
0.8322	Intermediate Similarity	NPC474621
0.8322	Intermediate Similarity	NPC135524
0.8322	Intermediate Similarity	NPC474622
0.8322	Intermediate Similarity	NPC474961
0.8321	Intermediate Similarity	NPC17083
0.8309	Intermediate Similarity	NPC92624
0.8309	Intermediate Similarity	NPC278928
0.8298	Intermediate Similarity	NPC4214
0.8298	Intermediate Similarity	NPC20210
0.8296	Intermediate Similarity	NPC72667
0.8288	Intermediate Similarity	NPC119767
0.8288	Intermediate Similarity	NPC472135
0.8286	Intermediate Similarity	NPC141934
0.8278	Intermediate Similarity	NPC317580
0.8273	Intermediate Similarity	NPC44437
0.8271	Intermediate Similarity	NPC275145
0.8267	Intermediate Similarity	NPC318270
0.8261	Intermediate Similarity	NPC110609
0.8261	Intermediate Similarity	NPC246693
0.8261	Intermediate Similarity	NPC242358
0.8258	Intermediate Similarity	NPC154696
0.8252	Intermediate Similarity	NPC305845
0.8252	Intermediate Similarity	NPC187843
0.8252	Intermediate Similarity	NPC204045
0.8248	Intermediate Similarity	NPC108129
0.8248	Intermediate Similarity	NPC259942
0.8248	Intermediate Similarity	NPC475741
0.8244	Intermediate Similarity	NPC206778
0.8244	Intermediate Similarity	NPC285829
0.8239	Intermediate Similarity	NPC143438
0.8231	Intermediate Similarity	NPC142846
0.8227	Intermediate Similarity	NPC49911
0.8224	Intermediate Similarity	NPC326084
0.8222	Intermediate Similarity	NPC227741
0.8222	Intermediate Similarity	NPC254492
0.8222	Intermediate Similarity	NPC295202
0.8222	Intermediate Similarity	NPC49647
0.8222	Intermediate Similarity	NPC136342
0.8219	Intermediate Similarity	NPC314437
0.8219	Intermediate Similarity	NPC143685
0.8214	Intermediate Similarity	NPC290803
0.8214	Intermediate Similarity	NPC258502
0.8209	Intermediate Similarity	NPC164014
0.8209	Intermediate Similarity	NPC236189
0.8207	Intermediate Similarity	NPC79627
0.8207	Intermediate Similarity	NPC193703
0.8207	Intermediate Similarity	NPC21599
0.82	Intermediate Similarity	NPC470408
0.82	Intermediate Similarity	NPC182921
0.82	Intermediate Similarity	NPC474824
0.82	Intermediate Similarity	NPC218870
0.8195	Intermediate Similarity	NPC244351
0.8195	Intermediate Similarity	NPC282577
0.8188	Intermediate Similarity	NPC477276
0.8188	Intermediate Similarity	NPC471851
0.8182	Intermediate Similarity	NPC32322

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 NPC161964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	958
0.2-0.3	1224
0.3-0.4	2723
0.4-0.5	2236
0.5-0.6	1191
0.6-0.7	392
0.7-0.8	74
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8993	High Similarity	NPD7390	Discontinued
0.8976	High Similarity	NPD1201	Approved
0.8897	High Similarity	NPD5406	Approved
0.8897	High Similarity	NPD5405	Approved
0.8897	High Similarity	NPD5408	Approved
0.8897	High Similarity	NPD5404	Approved
0.8846	High Similarity	NPD1470	Approved
0.8531	High Similarity	NPD7422	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7003	Approved
0.7939	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD3300	Phase 2
0.7885	Intermediate Similarity	NPD6959	Discontinued
0.7836	Intermediate Similarity	NPD3019	Approved
0.7815	Intermediate Similarity	NPD3226	Approved
0.7793	Intermediate Similarity	NPD2346	Discontinued
0.7704	Intermediate Similarity	NPD2932	Approved
0.7683	Intermediate Similarity	NPD8313	Approved
0.7683	Intermediate Similarity	NPD8312	Approved
0.7656	Intermediate Similarity	NPD2342	Discontinued
0.7578	Intermediate Similarity	NPD7473	Discontinued
0.7571	Intermediate Similarity	NPD2798	Approved
0.7534	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5951	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD1164	Approved
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD3764	Approved
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7468	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2799	Discontinued
0.7405	Intermediate Similarity	NPD7768	Phase 2
0.74	Intermediate Similarity	NPD8166	Discontinued
0.7391	Intermediate Similarity	NPD3023	Approved
0.7391	Intermediate Similarity	NPD3026	Approved
0.7372	Intermediate Similarity	NPD3025	Approved
0.7372	Intermediate Similarity	NPD3024	Approved
0.732	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1607	Approved
0.7278	Intermediate Similarity	NPD7819	Suspended
0.7246	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2313	Discontinued
0.7235	Intermediate Similarity	NPD8150	Discontinued
0.7233	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7177	Discontinued
0.7183	Intermediate Similarity	NPD1283	Approved
0.7181	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1510	Phase 2
0.7172	Intermediate Similarity	NPD7008	Discontinued
0.7171	Intermediate Similarity	NPD3750	Approved
0.717	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7411	Suspended
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4750	Phase 3
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7122	Intermediate Similarity	NPD1651	Approved
0.7097	Intermediate Similarity	NPD2533	Approved
0.7097	Intermediate Similarity	NPD2532	Approved
0.7097	Intermediate Similarity	NPD2534	Approved
0.7089	Intermediate Similarity	NPD4380	Phase 2
0.7087	Intermediate Similarity	NPD288	Approved
0.7086	Intermediate Similarity	NPD2344	Approved
0.7075	Intermediate Similarity	NPD6663	Approved
0.7069	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9266	Approved
0.7068	Intermediate Similarity	NPD74	Approved
0.7051	Intermediate Similarity	NPD6273	Approved
0.7042	Intermediate Similarity	NPD4878	Approved
0.7034	Intermediate Similarity	NPD5736	Approved
0.7029	Intermediate Similarity	NPD9493	Approved
0.702	Intermediate Similarity	NPD6100	Approved
0.702	Intermediate Similarity	NPD6099	Approved
0.7008	Intermediate Similarity	NPD844	Approved
0.6992	Remote Similarity	NPD9263	Approved
0.6992	Remote Similarity	NPD9267	Approved
0.6992	Remote Similarity	NPD9264	Approved
0.6988	Remote Similarity	NPD6166	Phase 2
0.6988	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3020	Approved
0.6974	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1281	Approved
0.6964	Remote Similarity	NPD5844	Phase 1
0.695	Remote Similarity	NPD2286	Discontinued
0.695	Remote Similarity	NPD4626	Approved
0.6948	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1929	Approved
0.6947	Remote Similarity	NPD1930	Approved
0.6947	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5027	Approved
0.6941	Remote Similarity	NPD5029	Approved
0.6941	Remote Similarity	NPD5031	Approved
0.6939	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4625	Phase 3
0.6934	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3091	Approved
0.6928	Remote Similarity	NPD1549	Phase 2
0.6923	Remote Similarity	NPD1511	Approved
0.6908	Remote Similarity	NPD1551	Phase 2
0.6906	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2309	Approved
0.6897	Remote Similarity	NPD1203	Approved
0.6897	Remote Similarity	NPD2797	Approved
0.6894	Remote Similarity	NPD1934	Approved
0.6893	Remote Similarity	NPD6535	Approved
0.6893	Remote Similarity	NPD6534	Approved
0.6892	Remote Similarity	NPD3268	Approved
0.6889	Remote Similarity	NPD3022	Approved
0.6889	Remote Similarity	NPD3021	Approved
0.6875	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6020	Phase 2
0.6857	Remote Similarity	NPD7610	Discontinued
0.6853	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3092	Approved
0.6852	Remote Similarity	NPD2801	Approved
0.685	Remote Similarity	NPD845	Approved
0.6842	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD3748	Approved
0.6842	Remote Similarity	NPD6559	Discontinued
0.6838	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6213	Phase 3
0.6836	Remote Similarity	NPD6212	Phase 3
0.6835	Remote Similarity	NPD1512	Approved
0.6831	Remote Similarity	NPD7870	Phase 2
0.6831	Remote Similarity	NPD7871	Phase 2
0.6831	Remote Similarity	NPD4059	Approved
0.6831	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7075	Discontinued
0.6828	Remote Similarity	NPD1876	Approved
0.6815	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3972	Approved
0.6806	Remote Similarity	NPD1608	Approved
0.6802	Remote Similarity	NPD5028	Approved
0.6802	Remote Similarity	NPD4955	Approved
0.6802	Remote Similarity	NPD36	Approved
0.6802	Remote Similarity	NPD4954	Approved
0.6802	Remote Similarity	NPD5026	Approved
0.6802	Remote Similarity	NPD5034	Approved
0.68	Remote Similarity	NPD2979	Phase 3
0.6797	Remote Similarity	NPD2796	Approved
0.6796	Remote Similarity	NPD6778	Approved
0.6796	Remote Similarity	NPD6782	Approved
0.6796	Remote Similarity	NPD6779	Approved
0.6796	Remote Similarity	NPD6781	Approved
0.6796	Remote Similarity	NPD6780	Approved
0.6796	Remote Similarity	NPD6776	Approved
0.6796	Remote Similarity	NPD6777	Approved
0.6781	Remote Similarity	NPD3094	Phase 2
0.6781	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD411	Approved
0.6779	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7699	Phase 2
0.6778	Remote Similarity	NPD7700	Phase 2
0.6763	Remote Similarity	NPD497	Approved
0.6763	Remote Similarity	NPD9281	Approved
0.6761	Remote Similarity	NPD4093	Discontinued
0.6753	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1471	Phase 3
0.6748	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5494	Approved
0.6744	Remote Similarity	NPD2859	Approved
0.6744	Remote Similarity	NPD5030	Phase 2
0.6744	Remote Similarity	NPD2860	Approved
0.6743	Remote Similarity	NPD5037	Approved
0.6743	Remote Similarity	NPD5038	Approved
0.6741	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD8320	Phase 1
0.6739	Remote Similarity	NPD8319	Approved
0.6731	Remote Similarity	NPD4628	Phase 3
0.6731	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6823	Phase 2
0.6718	Remote Similarity	NPD2066	Phase 3
0.6713	Remote Similarity	NPD3095	Discontinued
0.6711	Remote Similarity	NPD6651	Approved
0.6707	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD9261	Approved
0.6691	Remote Similarity	NPD498	Approved
0.6691	Remote Similarity	NPD495	Approved
0.6691	Remote Similarity	NPD496	Approved
0.669	Remote Similarity	NPD9717	Approved
0.6689	Remote Similarity	NPD4060	Phase 1
0.6686	Remote Similarity	NPD5036	Approved
0.6685	Remote Similarity	NPD7435	Discontinued
0.6685	Remote Similarity	NPD7696	Phase 3
0.6685	Remote Similarity	NPD7697	Approved
0.6685	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD6836	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