NPASS Compound

Structure

NPC215593 OpenBabel07101718202D 26 32 0 0 1 0 0 0 0 0999 V2000 1.2205 2.6553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7711 0.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8574 2.2211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6371 1.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5260 2.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9051 1.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7998 1.4524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6371 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4684 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9051 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0391 2.8452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1685 1.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1053 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7711 2.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9791 0.5653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7711 3.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0391 3.8452 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0424 0.5653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9051 4.3452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4684 0.3193 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6260 0.8891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5032 2.8452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7610 -0.0582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6371 4.3452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0391 4.8452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 7 13 2 0 0 0 0 7 21 1 0 0 0 0 8 14 2 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 5 1 1 0 0 0 11 17 1 0 0 0 0 12 6 1 1 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 23 2 0 0 0 0 16 24 2 0 0 0 0 17 19 1 0 0 0 0 17 25 1 6 0 0 0 18 20 1 0 0 0 0 18 26 1 6 0 0 0 19 16 1 6 0 0 0 19 25 1 0 0 0 0 20 15 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.06
Volume:	326.231
LogP:	4.107
LogD:	2.154
LogS:	-7.292
# Rotatable Bonds:	0
TPSA:	105.98
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	4.925
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.201
MDCK Permeability:	3.99941473006038e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.608
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	93.03125762939453%
Volume Distribution (VD):	0.552
Pgp-substrate:	8.480840682983398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.67
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.418
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.583
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	1.243
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.813
Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.89
Carcinogencity:	0.632
Eye Corrosion:	0.004
Eye Irritation:	0.723
Respiratory Toxicity:	0.297

Download Data

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

Natural Product: NPC215593

Natural Product ID:	NPC215593
*Common Name:**	CJGDIPRCPKGNLW-AHYXFKKWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CJGDIPRCPKGNLW-AHYXFKKWSA-N
Standard InCHI:	InChI=1S/C20H12O6/c21-7-3-1-5-9-12(18-20(26-18)15(23)13(7)9)6-2-4-8(22)14-10(6)11(5)17-19(25-17)16(14)24/h1-4,11-12,17-22H/t11-,12-,17+,18+,19-,20-/m0/s1
SMILES:	O=C1[C@@H]2O[C@@H]2[C@@H]2c3c1c(O)ccc3[C@H]1c3c2ccc(c3C(=O)[C@H]2[C@@H]1O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338990
PubChem CID:	114895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO33081	alternaria tenuissima que1se	Species	Pleosporaceae	Eukaryota	endophyte of Quercus emoryi	n.a.	n.a.	PMID[25260957]

☑ 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
Others	2

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Ratio CC50/IC50	=	15.0	n.a.	PMID[529606]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	290.0	nM	PMID[529606]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	97.0	%	PMID[529606]

☑ 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 NPC215593 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	409
0.1-0.2	1604
0.2-0.3	3494
0.3-0.4	9394
0.4-0.5	9958
0.5-0.6	5651
0.6-0.7	8610
0.7-0.8	3519
0.8-0.85	49
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9648	High Similarity	NPC472134
0.958	High Similarity	NPC472135
0.9514	High Similarity	NPC142846
0.8836	High Similarity	NPC85310
0.8759	High Similarity	NPC114620
0.8759	High Similarity	NPC103337
0.8707	High Similarity	NPC308572
0.8707	High Similarity	NPC469520
0.8636	High Similarity	NPC478133
0.8591	High Similarity	NPC84568
0.8591	High Similarity	NPC48130
0.8591	High Similarity	NPC218866
0.8591	High Similarity	NPC300684
0.8543	High Similarity	NPC119767
0.8533	High Similarity	NPC170055
0.8516	High Similarity	NPC314257
0.8491	Intermediate Similarity	NPC290160
0.8431	Intermediate Similarity	NPC477221
0.8431	Intermediate Similarity	NPC120171
0.8418	Intermediate Similarity	NPC184326
0.8418	Intermediate Similarity	NPC292863
0.8414	Intermediate Similarity	NPC472262
0.8414	Intermediate Similarity	NPC287604
0.8414	Intermediate Similarity	NPC161964
0.84	Intermediate Similarity	NPC313047
0.84	Intermediate Similarity	NPC474203
0.84	Intermediate Similarity	NPC295712
0.84	Intermediate Similarity	NPC451542
0.8389	Intermediate Similarity	NPC477275
0.8389	Intermediate Similarity	NPC106519
0.8389	Intermediate Similarity	NPC91019
0.8366	Intermediate Similarity	NPC290695
0.8366	Intermediate Similarity	NPC106524
0.8365	Intermediate Similarity	NPC137232
0.8365	Intermediate Similarity	NPC18380
0.8365	Intermediate Similarity	NPC478134
0.8355	Intermediate Similarity	NPC285122
0.8355	Intermediate Similarity	NPC147250
0.8354	Intermediate Similarity	NPC195167
0.8345	Intermediate Similarity	NPC52407
0.8345	Intermediate Similarity	NPC314048
0.8344	Intermediate Similarity	NPC471906
0.8333	Intermediate Similarity	NPC474517
0.8333	Intermediate Similarity	NPC239136
0.8333	Intermediate Similarity	NPC72669
0.8333	Intermediate Similarity	NPC19631
0.8323	Intermediate Similarity	NPC477276
0.8323	Intermediate Similarity	NPC205918
0.8312	Intermediate Similarity	NPC478219
0.8311	Intermediate Similarity	NPC13715
0.8301	Intermediate Similarity	NPC162751
0.8301	Intermediate Similarity	NPC52161
0.8301	Intermediate Similarity	NPC290194
0.828	Intermediate Similarity	NPC266469
0.8278	Intermediate Similarity	NPC174905
0.8278	Intermediate Similarity	NPC296752
0.8278	Intermediate Similarity	NPC293545
0.8276	Intermediate Similarity	NPC70622
0.8267	Intermediate Similarity	NPC110810
0.8247	Intermediate Similarity	NPC94781
0.8224	Intermediate Similarity	NPC477913
0.8224	Intermediate Similarity	NPC79627
0.8224	Intermediate Similarity	NPC227841
0.8217	Intermediate Similarity	NPC474824
0.8217	Intermediate Similarity	NPC182921
0.8217	Intermediate Similarity	NPC470408
0.8217	Intermediate Similarity	NPC218870
0.8212	Intermediate Similarity	NPC257644
0.8212	Intermediate Similarity	NPC474961
0.82	Intermediate Similarity	NPC225243
0.8194	Intermediate Similarity	NPC99731
0.8182	Intermediate Similarity	NPC5568
0.817	Intermediate Similarity	NPC478160
0.8158	Intermediate Similarity	NPC471682
0.8158	Intermediate Similarity	NPC354984
0.8146	Intermediate Similarity	NPC305845
0.8146	Intermediate Similarity	NPC204045
0.8141	Intermediate Similarity	NPC477914
0.8141	Intermediate Similarity	NPC315520
0.8138	Intermediate Similarity	NPC199253
0.8138	Intermediate Similarity	NPC136588
0.8133	Intermediate Similarity	NPC190457
0.8133	Intermediate Similarity	NPC26924
0.8121	Intermediate Similarity	NPC261292
0.8121	Intermediate Similarity	NPC301915
0.8121	Intermediate Similarity	NPC305060
0.8117	Intermediate Similarity	NPC470570
0.8113	Intermediate Similarity	NPC474861
0.8108	Intermediate Similarity	NPC80035
0.8108	Intermediate Similarity	NPC283088
0.8105	Intermediate Similarity	NPC21599
0.8105	Intermediate Similarity	NPC244691
0.8105	Intermediate Similarity	NPC193703
0.8105	Intermediate Similarity	NPC48762
0.8105	Intermediate Similarity	NPC29932
0.8101	Intermediate Similarity	NPC209393
0.8101	Intermediate Similarity	NPC205172
0.8101	Intermediate Similarity	NPC478218
0.8101	Intermediate Similarity	NPC472211
0.8099	Intermediate Similarity	NPC173978
0.8095	Intermediate Similarity	NPC225051
0.8095	Intermediate Similarity	NPC267205
0.8095	Intermediate Similarity	NPC78307
0.8092	Intermediate Similarity	NPC137649
0.8092	Intermediate Similarity	NPC135524
0.8086	Intermediate Similarity	NPC478229
0.8086	Intermediate Similarity	NPC315772
0.8082	Intermediate Similarity	NPC41847
0.8079	Intermediate Similarity	NPC315578
0.8079	Intermediate Similarity	NPC181560
0.8079	Intermediate Similarity	NPC169452
0.8077	Intermediate Similarity	NPC280753
0.8077	Intermediate Similarity	NPC44378
0.8075	Intermediate Similarity	NPC284495
0.8067	Intermediate Similarity	NPC173980
0.8065	Intermediate Similarity	NPC37709
0.8061	Intermediate Similarity	NPC300307
0.8054	Intermediate Similarity	NPC191976
0.8054	Intermediate Similarity	NPC155211
0.8054	Intermediate Similarity	NPC474813
0.8054	Intermediate Similarity	NPC86524
0.8052	Intermediate Similarity	NPC474630
0.8052	Intermediate Similarity	NPC34482
0.8052	Intermediate Similarity	NPC12402
0.8052	Intermediate Similarity	NPC471683
0.805	Intermediate Similarity	NPC82190
0.805	Intermediate Similarity	NPC192219
0.805	Intermediate Similarity	NPC174599
0.8042	Intermediate Similarity	NPC103540
0.8041	Intermediate Similarity	NPC50924
0.8041	Intermediate Similarity	NPC44437
0.8039	Intermediate Similarity	NPC100242
0.8039	Intermediate Similarity	NPC478164
0.8038	Intermediate Similarity	NPC474534
0.8038	Intermediate Similarity	NPC474533
0.8027	Intermediate Similarity	NPC478190
0.8027	Intermediate Similarity	NPC309430
0.8027	Intermediate Similarity	NPC17843
0.8026	Intermediate Similarity	NPC246638
0.8025	Intermediate Similarity	NPC205766
0.8025	Intermediate Similarity	NPC316457
0.8025	Intermediate Similarity	NPC472261
0.8013	Intermediate Similarity	NPC138099
0.8013	Intermediate Similarity	NPC242994
0.8012	Intermediate Similarity	NPC53139
0.8012	Intermediate Similarity	NPC295090
0.8	Intermediate Similarity	NPC53414
0.8	Intermediate Similarity	NPC283480
0.8	Intermediate Similarity	NPC143685
0.8	Intermediate Similarity	NPC53206
0.8	Intermediate Similarity	NPC245923
0.8	Intermediate Similarity	NPC51513
0.8	Intermediate Similarity	NPC148323
0.8	Intermediate Similarity	NPC478223
0.8	Intermediate Similarity	NPC202112
0.8	Intermediate Similarity	NPC282923
0.8	Intermediate Similarity	NPC475957
0.8	Intermediate Similarity	NPC471905
0.8	Intermediate Similarity	NPC247250
0.8	Intermediate Similarity	NPC767
0.8	Intermediate Similarity	NPC136878
0.8	Intermediate Similarity	NPC314437
0.7987	Intermediate Similarity	NPC70859
0.7987	Intermediate Similarity	NPC283590
0.7987	Intermediate Similarity	NPC61153
0.7987	Intermediate Similarity	NPC130899
0.7975	Intermediate Similarity	NPC187934
0.7975	Intermediate Similarity	NPC97637
0.7975	Intermediate Similarity	NPC15374
0.7974	Intermediate Similarity	NPC474300
0.7974	Intermediate Similarity	NPC193555
0.7974	Intermediate Similarity	NPC73061
0.7973	Intermediate Similarity	NPC115458
0.7973	Intermediate Similarity	NPC171968
0.7972	Intermediate Similarity	NPC234890
0.7972	Intermediate Similarity	NPC74507
0.7964	Intermediate Similarity	NPC4200
0.7962	Intermediate Similarity	NPC329933
0.7961	Intermediate Similarity	NPC168471
0.7961	Intermediate Similarity	NPC155205
0.7961	Intermediate Similarity	NPC96421
0.7959	Intermediate Similarity	NPC93015
0.7959	Intermediate Similarity	NPC205992
0.7959	Intermediate Similarity	NPC244699
0.7959	Intermediate Similarity	NPC85342
0.7959	Intermediate Similarity	NPC471851
0.7952	Intermediate Similarity	NPC175477
0.795	Intermediate Similarity	NPC317580
0.7949	Intermediate Similarity	NPC478018
0.7949	Intermediate Similarity	NPC476821
0.7947	Intermediate Similarity	NPC61398
0.7947	Intermediate Similarity	NPC416
0.7945	Intermediate Similarity	NPC276238
0.7937	Intermediate Similarity	NPC3449
0.7937	Intermediate Similarity	NPC66029
0.7937	Intermediate Similarity	NPC474501
0.7933	Intermediate Similarity	NPC254847
0.7933	Intermediate Similarity	NPC291454
0.7933	Intermediate Similarity	NPC272268
0.7933	Intermediate Similarity	NPC38158

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 NPC215593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	967
0.2-0.3	1569
0.3-0.4	2885
0.4-0.5	2002
0.5-0.6	1006
0.6-0.7	322
0.7-0.8	39
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8224	Intermediate Similarity	NPD7390	Discontinued
0.8143	Intermediate Similarity	NPD1201	Approved
0.8042	Intermediate Similarity	NPD1470	Approved
0.7933	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6959	Discontinued
0.7881	Intermediate Similarity	NPD5405	Approved
0.7881	Intermediate Similarity	NPD5404	Approved
0.7881	Intermediate Similarity	NPD5408	Approved
0.7881	Intermediate Similarity	NPD5406	Approved
0.7821	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3300	Phase 2
0.7578	Intermediate Similarity	NPD4380	Phase 2
0.7546	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7484	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD1510	Phase 2
0.7456	Intermediate Similarity	NPD6166	Phase 2
0.7456	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3787	Discontinued
0.7439	Intermediate Similarity	NPD7819	Suspended
0.7436	Intermediate Similarity	NPD1549	Phase 2
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7412	Intermediate Similarity	NPD7473	Discontinued
0.741	Intermediate Similarity	NPD7075	Discontinued
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1934	Approved
0.7355	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7003	Approved
0.7337	Intermediate Similarity	NPD6232	Discontinued
0.7333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1512	Approved
0.7326	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD943	Approved
0.7303	Intermediate Similarity	NPD3764	Approved
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7261	Intermediate Similarity	NPD2346	Discontinued
0.7251	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6535	Approved
0.7238	Intermediate Similarity	NPD6534	Approved
0.7233	Intermediate Similarity	NPD8166	Discontinued
0.7226	Intermediate Similarity	NPD1607	Approved
0.7222	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7411	Suspended
0.7208	Intermediate Similarity	NPD1240	Approved
0.7205	Intermediate Similarity	NPD1511	Approved
0.7197	Intermediate Similarity	NPD2935	Discontinued
0.7169	Intermediate Similarity	NPD6801	Discontinued
0.7166	Intermediate Similarity	NPD8320	Phase 1
0.7166	Intermediate Similarity	NPD8319	Approved
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD3019	Approved
0.7135	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD6782	Approved
0.7135	Intermediate Similarity	NPD6779	Approved
0.7135	Intermediate Similarity	NPD6781	Approved
0.7135	Intermediate Similarity	NPD6778	Approved
0.7135	Intermediate Similarity	NPD6780	Approved
0.7135	Intermediate Similarity	NPD6776	Approved
0.7134	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7125	Intermediate Similarity	NPD3750	Approved
0.712	Intermediate Similarity	NPD7699	Phase 2
0.712	Intermediate Similarity	NPD7700	Phase 2
0.7118	Intermediate Similarity	NPD5494	Approved
0.7112	Intermediate Similarity	NPD7435	Discontinued
0.7102	Intermediate Similarity	NPD7251	Discontinued
0.7101	Intermediate Similarity	NPD3749	Approved
0.7101	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2796	Approved
0.7086	Intermediate Similarity	NPD1164	Approved
0.7083	Intermediate Similarity	NPD3817	Phase 2
0.7081	Intermediate Similarity	NPD6190	Approved
0.7074	Intermediate Similarity	NPD7870	Phase 2
0.7074	Intermediate Similarity	NPD7871	Phase 2
0.7062	Intermediate Similarity	NPD7808	Phase 3
0.7048	Intermediate Similarity	NPD6599	Discontinued
0.7037	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6663	Approved
0.7027	Intermediate Similarity	NPD2932	Approved
0.7025	Intermediate Similarity	NPD2799	Discontinued
0.7024	Intermediate Similarity	NPD2801	Approved
0.7021	Intermediate Similarity	NPD7697	Approved
0.7021	Intermediate Similarity	NPD7698	Approved
0.7021	Intermediate Similarity	NPD7696	Phase 3
0.7012	Intermediate Similarity	NPD6273	Approved
0.6994	Remote Similarity	NPD6799	Approved
0.6993	Remote Similarity	NPD5736	Approved
0.6989	Remote Similarity	NPD7074	Phase 3
0.6982	Remote Similarity	NPD5402	Approved
0.6968	Remote Similarity	NPD2313	Discontinued
0.6966	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2344	Approved
0.6937	Remote Similarity	NPD1471	Phase 3
0.6932	Remote Similarity	NPD7054	Approved
0.6914	Remote Similarity	NPD4628	Phase 3
0.6902	Remote Similarity	NPD6213	Phase 3
0.6902	Remote Similarity	NPD6212	Phase 3
0.6902	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7472	Approved
0.6892	Remote Similarity	NPD9545	Approved
0.6891	Remote Similarity	NPD7874	Approved
0.6891	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD7701	Phase 2
0.6875	Remote Similarity	NPD3818	Discontinued
0.6875	Remote Similarity	NPD7177	Discontinued
0.6867	Remote Similarity	NPD5403	Approved
0.6856	Remote Similarity	NPD7801	Approved
0.6852	Remote Similarity	NPD2800	Approved
0.6851	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5401	Approved
0.6846	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7236	Approved
0.6821	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2798	Approved
0.6816	Remote Similarity	NPD6559	Discontinued
0.6813	Remote Similarity	NPD3748	Approved
0.6797	Remote Similarity	NPD1283	Approved
0.6778	Remote Similarity	NPD5026	Approved
0.6778	Remote Similarity	NPD5028	Approved
0.6778	Remote Similarity	NPD4954	Approved
0.6778	Remote Similarity	NPD36	Approved
0.6778	Remote Similarity	NPD4955	Approved
0.6778	Remote Similarity	NPD5034	Approved
0.677	Remote Similarity	NPD1551	Phase 2
0.6768	Remote Similarity	NPD2309	Approved
0.6755	Remote Similarity	NPD3026	Approved
0.6755	Remote Similarity	NPD3023	Approved
0.6753	Remote Similarity	NPD8151	Discontinued
0.6743	Remote Similarity	NPD5710	Approved
0.6743	Remote Similarity	NPD5711	Approved
0.6733	Remote Similarity	NPD3025	Approved
0.6733	Remote Similarity	NPD3024	Approved
0.6722	Remote Similarity	NPD5030	Phase 2
0.6721	Remote Similarity	NPD5038	Approved
0.6721	Remote Similarity	NPD5037	Approved
0.6713	Remote Similarity	NPD2342	Discontinued
0.6702	Remote Similarity	NPD6823	Phase 2
0.6687	Remote Similarity	NPD6651	Approved
0.6686	Remote Similarity	NPD1247	Approved
0.6686	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD919	Approved
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD5036	Approved
0.6646	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3094	Phase 2
0.6634	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8285	Discontinued
0.663	Remote Similarity	NPD5027	Approved
0.663	Remote Similarity	NPD8434	Phase 2
0.663	Remote Similarity	NPD5031	Approved
0.663	Remote Similarity	NPD5029	Approved
0.6628	Remote Similarity	NPD8455	Phase 2
0.6628	Remote Similarity	NPD1465	Phase 2
0.6627	Remote Similarity	NPD7239	Suspended
0.6625	Remote Similarity	NPD230	Phase 1
0.6625	Remote Similarity	NPD6355	Discontinued
0.6623	Remote Similarity	NPD1651	Approved
0.662	Remote Similarity	NPD1237	Approved
0.6606	Remote Similarity	NPD3400	Discontinued
0.6603	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1281	Approved
0.6601	Remote Similarity	NPD3092	Approved
0.6599	Remote Similarity	NPD7635	Approved
0.6597	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4360	Phase 2
0.6596	Remote Similarity	NPD4363	Phase 3
0.6587	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7008	Discontinued
0.6581	Remote Similarity	NPD1876	Approved
0.6578	Remote Similarity	NPD5968	Phase 3
0.6571	Remote Similarity	NPD6234	Discontinued
0.657	Remote Similarity	NPD37	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