NPASS Compound

Structure

NPC472134 OpenBabel07101718292D 26 31 0 0 1 0 0 0 0 0999 V2000 3.8576 -2.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4945 -1.8759 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 3.1055 0.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1631 -1.9757 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 4.4369 -1.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6163 -0.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5948 -0.2201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1055 -1.2070 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 3.7424 -0.7728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -0.7728 0.0000 C 0 0 1 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 1.7321 -1.0000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2632 -0.5439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3981 0.4034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8130 0.4034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 6 1 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 12 2 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 8 21 1 0 0 0 0 9 16 2 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 10 23 2 0 0 0 0 11 15 1 0 0 0 0 11 24 1 6 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 15 12 1 1 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 13 1 1 0 0 0 17 19 1 0 0 0 0 18 25 2 0 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 18 1 6 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.08
Volume:	334.787
LogP:	2.521
LogD:	1.122
LogS:	-6.087
# Rotatable Bonds:	0
TPSA:	113.68
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	4.66
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.212
MDCK Permeability:	3.7921879538771464e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.379
Human Intestinal Absorption (HIA):	0.817
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	94.31953430175781%
Volume Distribution (VD):	0.511
Pgp-substrate:	8.054014205932617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.363
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.362
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	1.235
Half-life (T1/2):	0.63

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.759
Rat Oral Acute Toxicity:	0.357
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.713
Carcinogencity:	0.702
Eye Corrosion:	0.004
Eye Irritation:	0.571
Respiratory Toxicity:	0.575

Download Data

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

Natural Product: NPC472134

Natural Product ID:	NPC472134
*Common Name:**	JHMQRCUWXPACCR-XWEAYVSNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JHMQRCUWXPACCR-XWEAYVSNSA-N
Standard InCHI:	InChI=1S/C20H14O6/c21-8-3-1-6-7-2-4-9(22)16-13(7)17(19-20(26-19)18(16)25)15-11(24)5-10(23)14(8)12(6)15/h1-4,11,15,17,19-22,24H,5H2/t11-,15+,17-,19-,20+/m1/s1
SMILES:	O=C1C[C@@H](O)[C@H]2c3c1c(O)ccc3c1c3[C@H]2[C@H]2O[C@H]2C(=O)c3c(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338987
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002903] Perylenequinones

*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	=	50.0	n.a.	PMID[501654]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	90.0	nM	PMID[501654]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	97.0	%	PMID[501654]

☑ 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 NPC472134 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	391
0.1-0.2	1456
0.2-0.3	3093
0.3-0.4	8555
0.4-0.5	10852
0.5-0.6	5227
0.6-0.7	8202
0.7-0.8	4730
0.8-0.85	164
0.85-0.9	22
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC142846
0.9648	High Similarity	NPC472135
0.9648	High Similarity	NPC215593
0.9161	High Similarity	NPC85310
0.9028	High Similarity	NPC469520
0.869	High Similarity	NPC114620
0.869	High Similarity	NPC103337
0.8662	High Similarity	NPC290160
0.8649	High Similarity	NPC84568
0.8649	High Similarity	NPC218866
0.8649	High Similarity	NPC48130
0.8649	High Similarity	NPC300684
0.8639	High Similarity	NPC308572
0.8591	High Similarity	NPC170055
0.8571	High Similarity	NPC478133
0.8531	High Similarity	NPC314048
0.8487	Intermediate Similarity	NPC477221
0.8477	Intermediate Similarity	NPC290194
0.8477	Intermediate Similarity	NPC119767
0.8471	Intermediate Similarity	NPC184326
0.8471	Intermediate Similarity	NPC292863
0.8446	Intermediate Similarity	NPC91019
0.8446	Intermediate Similarity	NPC106519
0.8421	Intermediate Similarity	NPC106524
0.8421	Intermediate Similarity	NPC290695
0.8418	Intermediate Similarity	NPC18380
0.8418	Intermediate Similarity	NPC137232
0.8411	Intermediate Similarity	NPC285122
0.8408	Intermediate Similarity	NPC195167
0.8403	Intermediate Similarity	NPC52407
0.84	Intermediate Similarity	NPC471906
0.8392	Intermediate Similarity	NPC72669
0.8392	Intermediate Similarity	NPC474517
0.8389	Intermediate Similarity	NPC239136
0.8389	Intermediate Similarity	NPC19631
0.8377	Intermediate Similarity	NPC205918
0.8366	Intermediate Similarity	NPC478219
0.8366	Intermediate Similarity	NPC120171
0.8355	Intermediate Similarity	NPC52161
0.8355	Intermediate Similarity	NPC162751
0.8345	Intermediate Similarity	NPC472262
0.8345	Intermediate Similarity	NPC287604
0.8345	Intermediate Similarity	NPC161964
0.8344	Intermediate Similarity	NPC478160
0.8333	Intermediate Similarity	NPC314257
0.8333	Intermediate Similarity	NPC295712
0.8333	Intermediate Similarity	NPC474203
0.8333	Intermediate Similarity	NPC313047
0.8333	Intermediate Similarity	NPC451542
0.8333	Intermediate Similarity	NPC296752
0.8333	Intermediate Similarity	NPC70622
0.8333	Intermediate Similarity	NPC266469
0.8322	Intermediate Similarity	NPC477275
0.8322	Intermediate Similarity	NPC110810
0.8302	Intermediate Similarity	NPC478134
0.8289	Intermediate Similarity	NPC147250
0.8278	Intermediate Similarity	NPC227841
0.8278	Intermediate Similarity	NPC477913
0.8278	Intermediate Similarity	NPC79627
0.8269	Intermediate Similarity	NPC470408
0.8269	Intermediate Similarity	NPC218870
0.8269	Intermediate Similarity	NPC182921
0.8269	Intermediate Similarity	NPC472211
0.8269	Intermediate Similarity	NPC474824
0.8267	Intermediate Similarity	NPC474961
0.8258	Intermediate Similarity	NPC477276
0.8243	Intermediate Similarity	NPC13715
0.8212	Intermediate Similarity	NPC478164
0.8212	Intermediate Similarity	NPC174905
0.8212	Intermediate Similarity	NPC293545
0.82	Intermediate Similarity	NPC305845
0.82	Intermediate Similarity	NPC204045
0.8194	Intermediate Similarity	NPC136588
0.8194	Intermediate Similarity	NPC199253
0.8194	Intermediate Similarity	NPC477914
0.8188	Intermediate Similarity	NPC190457
0.8182	Intermediate Similarity	NPC94781
0.8176	Intermediate Similarity	NPC305060
0.817	Intermediate Similarity	NPC143685
0.8165	Intermediate Similarity	NPC474861
0.8163	Intermediate Similarity	NPC283088
0.8158	Intermediate Similarity	NPC29932
0.8158	Intermediate Similarity	NPC244691
0.8153	Intermediate Similarity	NPC478218
0.8153	Intermediate Similarity	NPC205172
0.8153	Intermediate Similarity	NPC209393
0.8151	Intermediate Similarity	NPC78307
0.8151	Intermediate Similarity	NPC225051
0.8146	Intermediate Similarity	NPC135524
0.8146	Intermediate Similarity	NPC137649
0.8146	Intermediate Similarity	NPC257644
0.8138	Intermediate Similarity	NPC41847
0.8137	Intermediate Similarity	NPC315772
0.8137	Intermediate Similarity	NPC478229
0.8137	Intermediate Similarity	NPC15374
0.8133	Intermediate Similarity	NPC225243
0.8125	Intermediate Similarity	NPC284495
0.8125	Intermediate Similarity	NPC99731
0.8121	Intermediate Similarity	NPC173980
0.8117	Intermediate Similarity	NPC37709
0.8117	Intermediate Similarity	NPC5568
0.811	Intermediate Similarity	NPC300307
0.8108	Intermediate Similarity	NPC474813
0.8108	Intermediate Similarity	NPC155211
0.8105	Intermediate Similarity	NPC12402
0.8101	Intermediate Similarity	NPC174599
0.8101	Intermediate Similarity	NPC82190
0.8101	Intermediate Similarity	NPC192219
0.8095	Intermediate Similarity	NPC50924
0.8092	Intermediate Similarity	NPC471682
0.8092	Intermediate Similarity	NPC354984
0.8089	Intermediate Similarity	NPC474534
0.8089	Intermediate Similarity	NPC474533
0.8082	Intermediate Similarity	NPC478190
0.8082	Intermediate Similarity	NPC17843
0.8079	Intermediate Similarity	NPC246638
0.8077	Intermediate Similarity	NPC205766
0.8077	Intermediate Similarity	NPC315520
0.8075	Intermediate Similarity	NPC219686
0.8075	Intermediate Similarity	NPC472261
0.8072	Intermediate Similarity	NPC470333
0.8067	Intermediate Similarity	NPC26924
0.8063	Intermediate Similarity	NPC472617
0.8063	Intermediate Similarity	NPC324736
0.8063	Intermediate Similarity	NPC228654
0.8063	Intermediate Similarity	NPC53139
0.8056	Intermediate Similarity	NPC247250
0.8056	Intermediate Similarity	NPC767
0.8054	Intermediate Similarity	NPC475957
0.8054	Intermediate Similarity	NPC245923
0.8054	Intermediate Similarity	NPC261292
0.8054	Intermediate Similarity	NPC301915
0.8052	Intermediate Similarity	NPC470570
0.8052	Intermediate Similarity	NPC136878
0.8052	Intermediate Similarity	NPC314437
0.805	Intermediate Similarity	NPC478223
0.805	Intermediate Similarity	NPC283480
0.805	Intermediate Similarity	NPC148323
0.8041	Intermediate Similarity	NPC61153
0.8041	Intermediate Similarity	NPC283590
0.8041	Intermediate Similarity	NPC80035
0.8041	Intermediate Similarity	NPC70859
0.8041	Intermediate Similarity	NPC130899
0.8039	Intermediate Similarity	NPC48762
0.8039	Intermediate Similarity	NPC21599
0.8039	Intermediate Similarity	NPC193703
0.8037	Intermediate Similarity	NPC469664
0.8028	Intermediate Similarity	NPC173978
0.8028	Intermediate Similarity	NPC234890
0.8028	Intermediate Similarity	NPC74507
0.8027	Intermediate Similarity	NPC267205
0.8025	Intermediate Similarity	NPC187934
0.8025	Intermediate Similarity	NPC97637
0.8014	Intermediate Similarity	NPC471851
0.8014	Intermediate Similarity	NPC244699
0.8014	Intermediate Similarity	NPC93015
0.8013	Intermediate Similarity	NPC168471
0.8013	Intermediate Similarity	NPC280753
0.8013	Intermediate Similarity	NPC329933
0.8013	Intermediate Similarity	NPC96421
0.8013	Intermediate Similarity	NPC169452
0.8013	Intermediate Similarity	NPC44378
0.8013	Intermediate Similarity	NPC315578
0.8013	Intermediate Similarity	NPC181560
0.8012	Intermediate Similarity	NPC4200
0.8012	Intermediate Similarity	NPC472618
0.8	Intermediate Similarity	NPC478018
0.8	Intermediate Similarity	NPC476821
0.8	Intermediate Similarity	NPC264063
0.8	Intermediate Similarity	NPC469486
0.8	Intermediate Similarity	NPC276238
0.7987	Intermediate Similarity	NPC191976
0.7987	Intermediate Similarity	NPC471683
0.7987	Intermediate Similarity	NPC474630
0.7987	Intermediate Similarity	NPC86524
0.7987	Intermediate Similarity	NPC66029
0.7987	Intermediate Similarity	NPC3449
0.7987	Intermediate Similarity	NPC34482
0.7975	Intermediate Similarity	NPC478220
0.7975	Intermediate Similarity	NPC87708
0.7974	Intermediate Similarity	NPC100242
0.7974	Intermediate Similarity	NPC143898
0.7973	Intermediate Similarity	NPC202225
0.7973	Intermediate Similarity	NPC44437
0.7972	Intermediate Similarity	NPC103540
0.7964	Intermediate Similarity	NPC470336
0.7964	Intermediate Similarity	NPC470335
0.7964	Intermediate Similarity	NPC229051
0.7962	Intermediate Similarity	NPC290954
0.7962	Intermediate Similarity	NPC255641
0.7962	Intermediate Similarity	NPC147735
0.7959	Intermediate Similarity	NPC309430
0.7952	Intermediate Similarity	NPC478021
0.795	Intermediate Similarity	NPC295090
0.7949	Intermediate Similarity	NPC473719
0.7947	Intermediate Similarity	NPC138099
0.7947	Intermediate Similarity	NPC242994
0.7945	Intermediate Similarity	NPC147757
0.7945	Intermediate Similarity	NPC31799
0.7945	Intermediate Similarity	NPC27659

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 NPC472134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	925
0.2-0.3	1600
0.3-0.4	2796
0.4-0.5	2017
0.5-0.6	1020
0.6-0.7	376
0.7-0.8	71
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8278	Intermediate Similarity	NPD7390	Discontinued
0.8075	Intermediate Similarity	NPD6959	Discontinued
0.8071	Intermediate Similarity	NPD1201	Approved
0.7972	Intermediate Similarity	NPD1470	Approved
0.7933	Intermediate Similarity	NPD5404	Approved
0.7933	Intermediate Similarity	NPD5406	Approved
0.7933	Intermediate Similarity	NPD5405	Approved
0.7933	Intermediate Similarity	NPD5408	Approved
0.7871	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4380	Phase 2
0.7557	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8150	Discontinued
0.7516	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7456	Intermediate Similarity	NPD7473	Discontinued
0.7453	Intermediate Similarity	NPD3226	Approved
0.7443	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3751	Discontinued
0.7403	Intermediate Similarity	NPD1510	Phase 2
0.7389	Intermediate Similarity	NPD7003	Approved
0.7381	Intermediate Similarity	NPD6232	Discontinued
0.7381	Intermediate Similarity	NPD3787	Discontinued
0.7378	Intermediate Similarity	NPD7819	Suspended
0.7372	Intermediate Similarity	NPD1549	Phase 2
0.7368	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7075	Discontinued
0.7317	Intermediate Similarity	NPD1934	Approved
0.7317	Intermediate Similarity	NPD6801	Discontinued
0.7294	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6535	Approved
0.7278	Intermediate Similarity	NPD6534	Approved
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD1512	Approved
0.7261	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD943	Approved
0.7239	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7237	Intermediate Similarity	NPD3764	Approved
0.7215	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2532	Approved
0.7205	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2533	Approved
0.7205	Intermediate Similarity	NPD2534	Approved
0.7204	Intermediate Similarity	NPD8320	Phase 1
0.7204	Intermediate Similarity	NPD8319	Approved
0.7197	Intermediate Similarity	NPD2346	Discontinued
0.7186	Intermediate Similarity	NPD7768	Phase 2
0.7184	Intermediate Similarity	NPD6797	Phase 2
0.7174	Intermediate Similarity	NPD6782	Approved
0.7174	Intermediate Similarity	NPD6779	Approved
0.7174	Intermediate Similarity	NPD6777	Approved
0.7174	Intermediate Similarity	NPD6776	Approved
0.7174	Intermediate Similarity	NPD6778	Approved
0.7174	Intermediate Similarity	NPD6781	Approved
0.7174	Intermediate Similarity	NPD6780	Approved
0.717	Intermediate Similarity	NPD8166	Discontinued
0.7161	Intermediate Similarity	NPD1607	Approved
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7411	Suspended
0.7151	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD2935	Discontinued
0.7133	Intermediate Similarity	NPD1164	Approved
0.7125	Intermediate Similarity	NPD6190	Approved
0.7112	Intermediate Similarity	NPD7871	Phase 2
0.7112	Intermediate Similarity	NPD7870	Phase 2
0.7102	Intermediate Similarity	NPD7808	Phase 3
0.7099	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3882	Suspended
0.7075	Intermediate Similarity	NPD3019	Approved
0.707	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3750	Approved
0.7059	Intermediate Similarity	NPD7696	Phase 3
0.7059	Intermediate Similarity	NPD7697	Approved
0.7059	Intermediate Similarity	NPD5494	Approved
0.7059	Intermediate Similarity	NPD7698	Approved
0.7055	Intermediate Similarity	NPD6273	Approved
0.7029	Intermediate Similarity	NPD7074	Phase 3
0.7025	Intermediate Similarity	NPD2796	Approved
0.7024	Intermediate Similarity	NPD5402	Approved
0.7024	Intermediate Similarity	NPD3817	Phase 2
0.7006	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6599	Discontinued
0.6984	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2344	Approved
0.6971	Remote Similarity	NPD7054	Approved
0.6968	Remote Similarity	NPD6663	Approved
0.6964	Remote Similarity	NPD2801	Approved
0.6962	Remote Similarity	NPD2799	Discontinued
0.6959	Remote Similarity	NPD2932	Approved
0.6957	Remote Similarity	NPD4628	Phase 3
0.6949	Remote Similarity	NPD6559	Discontinued
0.694	Remote Similarity	NPD6213	Phase 3
0.694	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6212	Phase 3
0.6933	Remote Similarity	NPD6799	Approved
0.6932	Remote Similarity	NPD7472	Approved
0.6928	Remote Similarity	NPD5736	Approved
0.6927	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7874	Approved
0.6914	Remote Similarity	NPD3818	Discontinued
0.6914	Remote Similarity	NPD7177	Discontinued
0.6911	Remote Similarity	NPD7701	Phase 2
0.6909	Remote Similarity	NPD5403	Approved
0.6903	Remote Similarity	NPD2313	Discontinued
0.6894	Remote Similarity	NPD2800	Approved
0.6891	Remote Similarity	NPD7801	Approved
0.689	Remote Similarity	NPD5401	Approved
0.6882	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8151	Discontinued
0.6875	Remote Similarity	NPD1471	Phase 3
0.6871	Remote Similarity	NPD7236	Approved
0.6842	Remote Similarity	NPD1283	Approved
0.6824	Remote Similarity	NPD9545	Approved
0.6816	Remote Similarity	NPD5026	Approved
0.6816	Remote Similarity	NPD5028	Approved
0.6816	Remote Similarity	NPD4954	Approved
0.6816	Remote Similarity	NPD4955	Approved
0.6816	Remote Similarity	NPD36	Approved
0.6816	Remote Similarity	NPD5034	Approved
0.6815	Remote Similarity	NPD4060	Phase 1
0.681	Remote Similarity	NPD2309	Approved
0.6796	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1465	Phase 2
0.6765	Remote Similarity	NPD8455	Phase 2
0.6761	Remote Similarity	NPD2342	Discontinued
0.676	Remote Similarity	NPD5030	Phase 2
0.6758	Remote Similarity	NPD5038	Approved
0.6758	Remote Similarity	NPD5037	Approved
0.6755	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2798	Approved
0.675	Remote Similarity	NPD3748	Approved
0.6748	Remote Similarity	NPD3400	Discontinued
0.6737	Remote Similarity	NPD6823	Phase 2
0.673	Remote Similarity	NPD6651	Approved
0.6724	Remote Similarity	NPD1247	Approved
0.6722	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3091	Approved
0.6709	Remote Similarity	NPD2979	Phase 3
0.6708	Remote Similarity	NPD1551	Phase 2
0.6707	Remote Similarity	NPD920	Approved
0.6705	Remote Similarity	NPD919	Approved
0.6703	Remote Similarity	NPD5036	Approved
0.6689	Remote Similarity	NPD3026	Approved
0.6689	Remote Similarity	NPD3023	Approved
0.6688	Remote Similarity	NPD3094	Phase 2
0.6686	Remote Similarity	NPD5711	Approved
0.6686	Remote Similarity	NPD5710	Approved
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7239	Suspended
0.6645	Remote Similarity	NPD1281	Approved
0.6645	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3092	Approved
0.6644	Remote Similarity	NPD7635	Approved
0.6633	Remote Similarity	NPD7783	Phase 2
0.6633	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD4360	Phase 2
0.6631	Remote Similarity	NPD4363	Phase 3
0.6628	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7008	Discontinued
0.6608	Remote Similarity	NPD37	Approved
0.6605	Remote Similarity	NPD6100	Approved
0.6605	Remote Similarity	NPD6099	Approved
0.6603	Remote Similarity	NPD2861	Phase 2
0.6601	Remote Similarity	NPD1608	Approved
0.6599	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5035	Approved
0.6591	Remote Similarity	NPD7229	Phase 3
0.659	Remote Similarity	NPD4965	Approved
0.659	Remote Similarity	NPD4967	Phase 2
0.659	Remote Similarity	NPD4966	Approved
0.6587	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6798	Discontinued
0.6575	Remote Similarity	NPD5031	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