NPASS Compound

Structure

NPC19631 OpenBabel07101719252D 38 43 0 0 0 0 0 0 0 0999 V2000 4.3301 -4.5000 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 -2.5981 1.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 -1.0000 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 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 6.0622 -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 5.1962 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 5.1962 -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 5.1962 -1.0000 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 -0.0000 2.0000 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 6.0622 -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 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 7.7942 -4.5000 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 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 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 6.9282 -1.0000 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 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 15 1 0 0 0 0 5 19 2 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 20 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 21 1 0 0 0 0 13 21 1 0 0 0 0 14 31 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 25 2 0 0 0 0 16 26 1 0 0 0 0 17 24 2 0 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 0 0 0 0 20 24 1 0 0 0 0 20 33 1 0 0 0 0 21 29 2 0 0 0 0 22 27 1 0 0 0 0 23 30 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 26 34 2 0 0 0 0 27 35 2 0 0 0 0 28 36 2 0 0 0 0 29 37 1 0 0 0 0 30 38 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.1
Volume:	504.236
LogP:	6.465
LogD:	2.451
LogS:	-5.445
# Rotatable Bonds:	0
TPSA:	155.52
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.136
Synthetic Accessibility Score:	3.727
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.33
MDCK Permeability:	4.636366611521225e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	93.51629638671875%
Volume Distribution (VD):	0.572
Pgp-substrate:	11.100397109985352%

ADMET: Metabolism

CYP1A2-inhibitor:	0.941
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.561
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	6.11
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.39
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.956
Carcinogencity:	0.788
Eye Corrosion:	0.003
Eye Irritation:	0.936
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC19631

Natural Product ID:	NPC19631
*Common Name:**	Microcarpin
IUPAC Name:	2-(4,6-dihydroxy-8-methyl-9,10-dioxoanthracen-2-yl)-1,8-dihydroxy-3-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	ZRRZSYXEHVZHQQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H18O8/c1-11-6-14(31)10-18-22(11)27(35)17-8-13(9-20(33)24(17)28(18)36)21-12(2)7-16-25(29(21)37)30(38)23-15(26(16)34)4-3-5-19(23)32/h3-10,31-33,37H,1-2H3
SMILES:	Oc1cc(C)c2c(c1)C(=O)c1c(C2=O)cc(cc1O)c1c(C)cc2c(c1O)C(=O)c1c(C2=O)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104735
PubChem CID:	76321113
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
NPO33246	kniphofia ensifolia	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24326280]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	60000.0	nM	PMID[518011]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10000.0	nM	PMID[518011]

☑ 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 NPC19631 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	400
0.1-0.2	1744
0.2-0.3	3932
0.3-0.4	10317
0.4-0.5	8616
0.5-0.6	5731
0.6-0.7	7337
0.7-0.8	4124
0.8-0.85	342
0.85-0.9	108
0.9-0.95	42
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239136
0.9504	High Similarity	NPC37709
0.9496	High Similarity	NPC471682
0.9496	High Similarity	NPC296752
0.9424	High Similarity	NPC257644
0.9362	High Similarity	NPC471683
0.9338	High Similarity	NPC283088
0.9333	High Similarity	NPC225051
0.9291	High Similarity	NPC227841
0.9275	High Similarity	NPC13715
0.9265	High Similarity	NPC287604
0.9265	High Similarity	NPC472262
0.9265	High Similarity	NPC161964
0.922	High Similarity	NPC295712
0.922	High Similarity	NPC174905
0.922	High Similarity	NPC474203
0.922	High Similarity	NPC293545
0.922	High Similarity	NPC313047
0.922	High Similarity	NPC451542
0.9214	High Similarity	NPC246638
0.9203	High Similarity	NPC245923
0.9185	High Similarity	NPC474517
0.9185	High Similarity	NPC72669
0.9143	High Similarity	NPC225243
0.913	High Similarity	NPC474813
0.913	High Similarity	NPC155211
0.9124	High Similarity	NPC50924
0.9097	High Similarity	NPC290194
0.9071	High Similarity	NPC242994
0.9071	High Similarity	NPC138099
0.9058	High Similarity	NPC80035
0.9037	High Similarity	NPC99731
0.9028	High Similarity	NPC271944
0.9028	High Similarity	NPC110882
0.9028	High Similarity	NPC85393
0.9021	High Similarity	NPC10764
0.9007	High Similarity	NPC181560
0.9007	High Similarity	NPC169452
0.9007	High Similarity	NPC96421
0.8963	High Similarity	NPC282923
0.8963	High Similarity	NPC48248
0.8958	High Similarity	NPC12402
0.8929	High Similarity	NPC471905
0.8929	High Similarity	NPC53206
0.8929	High Similarity	NPC62272
0.8929	High Similarity	NPC53414
0.8913	High Similarity	NPC115458
0.8912	High Similarity	NPC205766
0.8905	High Similarity	NPC244699
0.8881	High Similarity	NPC193555
0.8881	High Similarity	NPC85310
0.8865	High Similarity	NPC416
0.8865	High Similarity	NPC61398
0.8857	High Similarity	NPC254847
0.8851	High Similarity	NPC35
0.8844	High Similarity	NPC477221
0.8841	High Similarity	NPC58685
0.8816	High Similarity	NPC470342
0.8816	High Similarity	NPC472060
0.8816	High Similarity	NPC472052
0.88	High Similarity	NPC66029
0.88	High Similarity	NPC226656
0.88	High Similarity	NPC318270
0.88	High Similarity	NPC66508
0.8794	High Similarity	NPC44960
0.8794	High Similarity	NPC474110
0.8777	High Similarity	NPC52407
0.8777	High Similarity	NPC53896
0.8768	High Similarity	NPC205992
0.8767	High Similarity	NPC147250
0.8767	High Similarity	NPC314437
0.8759	High Similarity	NPC146647
0.8759	High Similarity	NPC34414
0.875	High Similarity	NPC469520
0.875	High Similarity	NPC135524
0.875	High Similarity	NPC69755
0.8741	High Similarity	NPC315578
0.8741	High Similarity	NPC103540
0.8732	High Similarity	NPC4214
0.8723	High Similarity	NPC272268
0.8723	High Similarity	NPC191976
0.8714	High Similarity	NPC166480
0.8714	High Similarity	NPC44437
0.8714	High Similarity	NPC282780
0.8707	High Similarity	NPC119767
0.8705	High Similarity	NPC70622
0.8696	High Similarity	NPC55949
0.8686	High Similarity	NPC96024
0.8684	High Similarity	NPC317580
0.8681	High Similarity	NPC305845
0.8681	High Similarity	NPC477275
0.8681	High Similarity	NPC204045
0.8675	High Similarity	NPC266469
0.8671	High Similarity	NPC26924
0.8671	High Similarity	NPC143438
0.8667	High Similarity	NPC142956
0.8667	High Similarity	NPC173978
0.8662	High Similarity	NPC53001
0.8658	High Similarity	NPC315520
0.8652	High Similarity	NPC258502
0.8643	High Similarity	NPC314048
0.8643	High Similarity	NPC267205
0.863	High Similarity	NPC193703
0.863	High Similarity	NPC21599
0.8627	High Similarity	NPC326084
0.8627	High Similarity	NPC324736
0.8623	High Similarity	NPC276238
0.8601	High Similarity	NPC87723
0.8593	High Similarity	NPC375356
0.8582	High Similarity	NPC12070
0.8582	High Similarity	NPC288089
0.8571	High Similarity	NPC475449
0.8571	High Similarity	NPC68441
0.8571	High Similarity	NPC34482
0.8561	High Similarity	NPC136588
0.8561	High Similarity	NPC199253
0.8542	High Similarity	NPC190457
0.854	High Similarity	NPC3224
0.8535	High Similarity	NPC477835
0.8521	High Similarity	NPC249272
0.8519	High Similarity	NPC91478
0.8519	High Similarity	NPC300274
0.8514	High Similarity	NPC470570
0.8511	High Similarity	NPC294226
0.8511	High Similarity	NPC114183
0.8503	High Similarity	NPC48762
0.8503	High Similarity	NPC471906
0.8503	High Similarity	NPC79627
0.8503	High Similarity	NPC244691
0.85	High Similarity	NPC93015
0.85	High Similarity	NPC41847
0.8493	Intermediate Similarity	NPC73061
0.8493	Intermediate Similarity	NPC474961
0.8487	Intermediate Similarity	NPC470408
0.8487	Intermediate Similarity	NPC218870
0.8487	Intermediate Similarity	NPC182921
0.8487	Intermediate Similarity	NPC474824
0.8478	Intermediate Similarity	NPC176130
0.8478	Intermediate Similarity	NPC78364
0.8478	Intermediate Similarity	NPC69424
0.8478	Intermediate Similarity	NPC84672
0.8462	Intermediate Similarity	NPC118919
0.8456	Intermediate Similarity	NPC472135
0.8451	Intermediate Similarity	NPC270899
0.8444	Intermediate Similarity	NPC120545
0.8435	Intermediate Similarity	NPC53016
0.8435	Intermediate Similarity	NPC66593
0.8429	Intermediate Similarity	NPC31799
0.8429	Intermediate Similarity	NPC108129
0.8425	Intermediate Similarity	NPC290550
0.8414	Intermediate Similarity	NPC1268
0.8411	Intermediate Similarity	NPC477914
0.8406	Intermediate Similarity	NPC160499
0.8406	Intermediate Similarity	NPC254492
0.8406	Intermediate Similarity	NPC96915
0.8406	Intermediate Similarity	NPC231774
0.8403	Intermediate Similarity	NPC305060
0.8403	Intermediate Similarity	NPC147418
0.84	Intermediate Similarity	NPC142846
0.8394	Intermediate Similarity	NPC199273
0.8389	Intermediate Similarity	NPC472134
0.8389	Intermediate Similarity	NPC143685
0.8389	Intermediate Similarity	NPC285122
0.8387	Intermediate Similarity	NPC177650
0.8382	Intermediate Similarity	NPC307174
0.8378	Intermediate Similarity	NPC477913
0.8377	Intermediate Similarity	NPC474861
0.8369	Intermediate Similarity	NPC17083
0.8357	Intermediate Similarity	NPC92624
0.8356	Intermediate Similarity	NPC203063
0.8345	Intermediate Similarity	NPC72667
0.8345	Intermediate Similarity	NPC20210
0.8333	Intermediate Similarity	NPC126767
0.8333	Intermediate Similarity	NPC118027
0.8333	Intermediate Similarity	NPC215593
0.8333	Intermediate Similarity	NPC315275
0.8333	Intermediate Similarity	NPC312929
0.8333	Intermediate Similarity	NPC186325
0.8333	Intermediate Similarity	NPC289042
0.8333	Intermediate Similarity	NPC245584
0.8333	Intermediate Similarity	NPC190648
0.8333	Intermediate Similarity	NPC312993
0.8333	Intermediate Similarity	NPC56433
0.8323	Intermediate Similarity	NPC477836
0.8322	Intermediate Similarity	NPC170055
0.8322	Intermediate Similarity	NPC202225
0.8322	Intermediate Similarity	NPC478019
0.8312	Intermediate Similarity	NPC254351
0.831	Intermediate Similarity	NPC175738
0.8299	Intermediate Similarity	NPC91019
0.8299	Intermediate Similarity	NPC124365
0.8299	Intermediate Similarity	NPC106519
0.8299	Intermediate Similarity	NPC187843
0.8298	Intermediate Similarity	NPC259942
0.8289	Intermediate Similarity	NPC255641
0.8289	Intermediate Similarity	NPC470568
0.8289	Intermediate Similarity	NPC290954
0.828	Intermediate Similarity	NPC189552
0.828	Intermediate Similarity	NPC273467
0.828	Intermediate Similarity	NPC472261

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 NPC19631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	975
0.2-0.3	1375
0.3-0.4	2836
0.4-0.5	2117
0.5-0.6	1037
0.6-0.7	343
0.7-0.8	79
0.8-0.85	4
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9291	High Similarity	NPD7390	Discontinued
0.8929	High Similarity	NPD5404	Approved
0.8929	High Similarity	NPD5405	Approved
0.8929	High Similarity	NPD5408	Approved
0.8929	High Similarity	NPD5406	Approved
0.8857	High Similarity	NPD1509	Clinical (unspecified phase)
0.8741	High Similarity	NPD1470	Approved
0.8571	High Similarity	NPD7422	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD1201	Approved
0.8165	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7987	Intermediate Similarity	NPD3226	Approved
0.7963	Intermediate Similarity	NPD7473	Discontinued
0.7933	Intermediate Similarity	NPD7003	Approved
0.7868	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD943	Approved
0.7727	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2344	Approved
0.7616	Intermediate Similarity	NPD2346	Discontinued
0.7569	Intermediate Similarity	NPD1164	Approved
0.7562	Intermediate Similarity	NPD7819	Suspended
0.7551	Intermediate Similarity	NPD3764	Approved
0.7532	Intermediate Similarity	NPD7458	Discontinued
0.7531	Intermediate Similarity	NPD3749	Approved
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7518	Intermediate Similarity	NPD3019	Approved
0.7516	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3300	Phase 2
0.7483	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7768	Phase 2
0.7467	Intermediate Similarity	NPD1607	Approved
0.7447	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7411	Suspended
0.7434	Intermediate Similarity	NPD2935	Discontinued
0.7429	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2932	Approved
0.7389	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4380	Phase 2
0.7368	Intermediate Similarity	NPD1510	Phase 2
0.7368	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD1240	Approved
0.7333	Intermediate Similarity	NPD2342	Discontinued
0.7299	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD7177	Discontinued
0.7278	Intermediate Similarity	NPD2534	Approved
0.7278	Intermediate Similarity	NPD2533	Approved
0.7278	Intermediate Similarity	NPD2532	Approved
0.7255	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6535	Approved
0.7247	Intermediate Similarity	NPD6534	Approved
0.7244	Intermediate Similarity	NPD8166	Discontinued
0.7239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5844	Phase 1
0.7214	Intermediate Similarity	NPD5951	Approved
0.7205	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7870	Phase 2
0.7174	Intermediate Similarity	NPD7871	Phase 2
0.7162	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD6777	Approved
0.7134	Intermediate Similarity	NPD3750	Approved
0.7127	Intermediate Similarity	NPD7700	Phase 2
0.7127	Intermediate Similarity	NPD7699	Phase 2
0.7115	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1549	Phase 2
0.7112	Intermediate Similarity	NPD8151	Discontinued
0.7108	Intermediate Similarity	NPD7075	Discontinued
0.7103	Intermediate Similarity	NPD3026	Approved
0.7103	Intermediate Similarity	NPD3023	Approved
0.7095	Intermediate Similarity	NPD6213	Phase 3
0.7095	Intermediate Similarity	NPD6212	Phase 3
0.7095	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2313	Discontinued
0.7083	Intermediate Similarity	NPD1651	Approved
0.7083	Intermediate Similarity	NPD3024	Approved
0.7083	Intermediate Similarity	NPD3025	Approved
0.7071	Intermediate Similarity	NPD7635	Approved
0.7051	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1471	Phase 3
0.7051	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2801	Approved
0.7027	Intermediate Similarity	NPD7698	Approved
0.7027	Intermediate Similarity	NPD1283	Approved
0.7027	Intermediate Similarity	NPD7697	Approved
0.7027	Intermediate Similarity	NPD7435	Discontinued
0.7027	Intermediate Similarity	NPD7696	Phase 3
0.702	Intermediate Similarity	NPD7008	Discontinued
0.7011	Intermediate Similarity	NPD6559	Discontinued
0.7007	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD1511	Approved
0.6989	Remote Similarity	NPD8320	Phase 1
0.6989	Remote Similarity	NPD8319	Approved
0.6987	Remote Similarity	NPD2796	Approved
0.697	Remote Similarity	NPD1934	Approved
0.6957	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3882	Suspended
0.6936	Remote Similarity	NPD6020	Phase 2
0.6928	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5494	Approved
0.6918	Remote Similarity	NPD2286	Discontinued
0.6918	Remote Similarity	NPD4628	Phase 3
0.6914	Remote Similarity	NPD6273	Approved
0.6914	Remote Similarity	NPD1512	Approved
0.6905	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4878	Approved
0.6886	Remote Similarity	NPD2296	Approved
0.6878	Remote Similarity	NPD7701	Phase 2
0.6867	Remote Similarity	NPD6801	Discontinued
0.6862	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2800	Approved
0.6852	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6599	Discontinued
0.6839	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1465	Phase 2
0.6824	Remote Similarity	NPD1281	Approved
0.6818	Remote Similarity	NPD5031	Approved
0.6818	Remote Similarity	NPD5027	Approved
0.6818	Remote Similarity	NPD5029	Approved
0.6818	Remote Similarity	NPD6663	Approved
0.6815	Remote Similarity	NPD3748	Approved
0.6806	Remote Similarity	NPD7874	Approved
0.6806	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4626	Approved
0.6802	Remote Similarity	NPD3926	Phase 2
0.68	Remote Similarity	NPD7074	Phase 3
0.68	Remote Similarity	NPD1876	Approved
0.6795	Remote Similarity	NPD6651	Approved
0.6791	Remote Similarity	NPD6823	Phase 2
0.6786	Remote Similarity	NPD74	Approved
0.6786	Remote Similarity	NPD9266	Approved
0.6783	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3818	Discontinued
0.6781	Remote Similarity	NPD9545	Approved
0.6776	Remote Similarity	NPD5736	Approved
0.6772	Remote Similarity	NPD6100	Approved
0.6772	Remote Similarity	NPD6099	Approved
0.6771	Remote Similarity	NPD7801	Approved
0.6761	Remote Similarity	NPD5953	Discontinued
0.6759	Remote Similarity	NPD9493	Approved
0.6744	Remote Similarity	NPD5710	Approved
0.6744	Remote Similarity	NPD5711	Approved
0.6743	Remote Similarity	NPD7054	Approved
0.673	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD9267	Approved
0.6714	Remote Similarity	NPD9264	Approved
0.6714	Remote Similarity	NPD9263	Approved
0.6708	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3400	Discontinued
0.6705	Remote Similarity	NPD7472	Approved
0.6691	Remote Similarity	NPD3020	Approved
0.6688	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4625	Phase 3
0.6687	Remote Similarity	NPD6799	Approved
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3751	Discontinued
0.6686	Remote Similarity	NPD3817	Phase 2
0.6685	Remote Similarity	NPD36	Approved
0.6685	Remote Similarity	NPD4954	Approved
0.6685	Remote Similarity	NPD5026	Approved
0.6685	Remote Similarity	NPD5028	Approved
0.6685	Remote Similarity	NPD4955	Approved
0.6685	Remote Similarity	NPD5034	Approved
0.6684	Remote Similarity	NPD7783	Phase 2
0.6684	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7654	Discontinued
0.6667	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD9269	Phase 2
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4287	Approved
0.6646	Remote Similarity	NPD1243	Approved
0.6645	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1203	Approved
0.6633	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5038	Approved
0.663	Remote Similarity	NPD5037	Approved
0.6629	Remote Similarity	NPD5030	Phase 2
0.6629	Remote Similarity	NPD7251	Discontinued
0.6627	Remote Similarity	NPD8455	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