NPASS Compound

Structure

CID327005 OpenBabel06191716192D 26 29 0 0 1 0 0 0 0 0999 V2000 0.0000 -1.0000 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 -3.4641 -0.0000 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 2.5981 -2.5000 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 -1.7321 -1.0000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 1.7321 -1.0000 0.0000 C 0 0 3 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 1.7321 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 25 2 0 0 0 0 18 26 1 0 0 0 0 19 21 2 0 0 0 0 20 21 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	351.15
Volume:	362.612
LogP:	3.938
LogD:	2.946
LogS:	-3.305
# Rotatable Bonds:	2
TPSA:	73.91
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.729
Synthetic Accessibility Score:	2.97
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.928
MDCK Permeability:	1.6360483641619794e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.722
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.104
Plasma Protein Binding (PPB):	95.43164825439453%
Volume Distribution (VD):	1.247
Pgp-substrate:	9.215669631958008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.519
CYP2D6-inhibitor:	0.733
CYP2D6-substrate:	0.661
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	5.131
Half-life (T1/2):	0.439

ADMET: Toxicity

hERG Blockers:	0.412
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.755
Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.918
Carcinogencity:	0.191
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC327005

Natural Product ID:	NPC327005
*Common Name:**	O-Demethylbuchenavianine
IUPAC Name:	5,7-dihydroxy-8-(1-methylpiperidin-2-yl)-2-phenylchromen-4-one
Synonyms:	O-Demethylbuchenavianine
Standard InCHIKey:	BBZGOLNDVQZCIH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H21NO4/c1-22-10-6-5-9-14(22)19-15(23)11-16(24)20-17(25)12-18(26-21(19)20)13-7-3-2-4-8-13/h2-4,7-8,11-12,14,23-24H,5-6,9-10H2,1H3
SMILES:	CN1CCCCC1c1c(O)cc(c2c1oc(cc2=O)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489967
PubChem CID:	5352072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

*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
NPO30062	Buchenavia capitata	Species	Combretaceae	Eukaryota	n.a.	Dominican Republic	n.a.	PMID[11430019]
NPO30062	Buchenavia capitata	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[1624941]

☑ 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
EC50	2
IC50	6
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	1
Organism	2
Others	2
Protein Complex	1
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	660.0	nM	PMID[476576]
NPT3932	Individual Protein	Dual specificity protein kinase CLK1	Mus musculus	IC50	=	8500.0	nM	PMID[476577]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	260.0	nM	PMID[476575]
NPT27	Others	Unspecified		TI	=	3.0	n.a.	PMID[476575]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	260.0	nM	PMID[476576]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	100.0	nM	PMID[476576]
NPT1509	Protein Complex	Cyclin-dependent kinase 5/CDK5 activator 1	Homo sapiens	IC50	=	1700.0	nM	PMID[476577]
NPT22078	PROTEIN FAMILY	Glycogen synthase kinase-3	Sus scrofa	IC50	=	5100.0	nM	PMID[476577]
NPT84	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Rattus norvegicus	IC50	>	10000.0	nM	PMID[476577]
NPT2	Others	Unspecified		IC50	=	90.0	nM	PMID[476577]

☑ 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 NPC327005 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	345
0.1-0.2	1697
0.2-0.3	6671
0.3-0.4	10961
0.4-0.5	4794
0.5-0.6	9171
0.6-0.7	6027
0.7-0.8	2988
0.8-0.85	42
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8488	Intermediate Similarity	NPC129578
0.8478	Intermediate Similarity	NPC15987
0.838	Intermediate Similarity	NPC469437
0.8295	Intermediate Similarity	NPC309692
0.8282	Intermediate Similarity	NPC219915
0.8282	Intermediate Similarity	NPC38219
0.8261	Intermediate Similarity	NPC303633
0.8261	Intermediate Similarity	NPC96565
0.8261	Intermediate Similarity	NPC220062
0.8261	Intermediate Similarity	NPC301217
0.8261	Intermediate Similarity	NPC55018
0.8261	Intermediate Similarity	NPC216978
0.8221	Intermediate Similarity	NPC59739
0.8221	Intermediate Similarity	NPC293852
0.8221	Intermediate Similarity	NPC217083
0.8221	Intermediate Similarity	NPC78803
0.8221	Intermediate Similarity	NPC299080
0.8221	Intermediate Similarity	NPC62840
0.8221	Intermediate Similarity	NPC214236
0.821	Intermediate Similarity	NPC159275
0.821	Intermediate Similarity	NPC270883
0.821	Intermediate Similarity	NPC69769
0.821	Intermediate Similarity	NPC172986
0.821	Intermediate Similarity	NPC261227
0.821	Intermediate Similarity	NPC241100
0.8199	Intermediate Similarity	NPC201395
0.8197	Intermediate Similarity	NPC264938
0.8182	Intermediate Similarity	NPC83357
0.8182	Intermediate Similarity	NPC470647
0.8182	Intermediate Similarity	NPC67805
0.8182	Intermediate Similarity	NPC142405
0.8182	Intermediate Similarity	NPC88964
0.8182	Intermediate Similarity	NPC214774
0.8182	Intermediate Similarity	NPC267375
0.8182	Intermediate Similarity	NPC301276
0.8182	Intermediate Similarity	NPC195621
0.8182	Intermediate Similarity	NPC312973
0.8182	Intermediate Similarity	NPC111786
0.8182	Intermediate Similarity	NPC20488
0.8182	Intermediate Similarity	NPC475052
0.8182	Intermediate Similarity	NPC246948
0.8182	Intermediate Similarity	NPC176229
0.8182	Intermediate Similarity	NPC54577
0.8177	Intermediate Similarity	NPC305542
0.8162	Intermediate Similarity	NPC234933
0.816	Intermediate Similarity	NPC156590
0.816	Intermediate Similarity	NPC110969
0.816	Intermediate Similarity	NPC118840
0.816	Intermediate Similarity	NPC205006
0.816	Intermediate Similarity	NPC14871
0.816	Intermediate Similarity	NPC282300
0.816	Intermediate Similarity	NPC64908
0.816	Intermediate Similarity	NPC147688
0.8148	Intermediate Similarity	NPC217186
0.8148	Intermediate Similarity	NPC78913
0.8148	Intermediate Similarity	NPC18260
0.8148	Intermediate Similarity	NPC53181
0.8135	Intermediate Similarity	NPC30749
0.8133	Intermediate Similarity	NPC23728
0.8133	Intermediate Similarity	NPC110303
0.8133	Intermediate Similarity	NPC473077
0.8133	Intermediate Similarity	NPC283234
0.8133	Intermediate Similarity	NPC296998
0.8121	Intermediate Similarity	NPC319752
0.811	Intermediate Similarity	NPC166482
0.811	Intermediate Similarity	NPC177354
0.811	Intermediate Similarity	NPC1089
0.811	Intermediate Similarity	NPC228504
0.811	Intermediate Similarity	NPC200694
0.811	Intermediate Similarity	NPC144499
0.811	Intermediate Similarity	NPC161506
0.811	Intermediate Similarity	NPC148757
0.811	Intermediate Similarity	NPC76338
0.811	Intermediate Similarity	NPC324134
0.811	Intermediate Similarity	NPC10937
0.811	Intermediate Similarity	NPC107572
0.811	Intermediate Similarity	NPC66515
0.811	Intermediate Similarity	NPC220998
0.811	Intermediate Similarity	NPC37496
0.811	Intermediate Similarity	NPC32739
0.811	Intermediate Similarity	NPC11561
0.811	Intermediate Similarity	NPC306829
0.811	Intermediate Similarity	NPC125855
0.811	Intermediate Similarity	NPC78
0.811	Intermediate Similarity	NPC166934
0.811	Intermediate Similarity	NPC167624
0.811	Intermediate Similarity	NPC227579
0.811	Intermediate Similarity	NPC194432
0.811	Intermediate Similarity	NPC328164
0.811	Intermediate Similarity	NPC265040
0.811	Intermediate Similarity	NPC226636
0.811	Intermediate Similarity	NPC182852
0.811	Intermediate Similarity	NPC64915
0.811	Intermediate Similarity	NPC296917
0.811	Intermediate Similarity	NPC324436
0.811	Intermediate Similarity	NPC40833
0.811	Intermediate Similarity	NPC76372
0.811	Intermediate Similarity	NPC223500
0.8105	Intermediate Similarity	NPC198160
0.8098	Intermediate Similarity	NPC150522
0.8098	Intermediate Similarity	NPC305355
0.8098	Intermediate Similarity	NPC475680
0.8098	Intermediate Similarity	NPC235239
0.8085	Intermediate Similarity	NPC288759
0.8084	Intermediate Similarity	NPC161191
0.8084	Intermediate Similarity	NPC132592
0.8084	Intermediate Similarity	NPC296869
0.8084	Intermediate Similarity	NPC160821
0.8077	Intermediate Similarity	NPC208890
0.8075	Intermediate Similarity	NPC13408
0.8072	Intermediate Similarity	NPC470132
0.8072	Intermediate Similarity	NPC470133
0.8072	Intermediate Similarity	NPC470131
0.8072	Intermediate Similarity	NPC476088
0.8072	Intermediate Similarity	NPC470134
0.8072	Intermediate Similarity	NPC109183
0.8072	Intermediate Similarity	NPC473078
0.8072	Intermediate Similarity	NPC474161
0.8065	Intermediate Similarity	NPC83019
0.8061	Intermediate Similarity	NPC9117
0.8061	Intermediate Similarity	NPC257097
0.8061	Intermediate Similarity	NPC223812
0.8061	Intermediate Similarity	NPC85162
0.8061	Intermediate Similarity	NPC150408
0.8061	Intermediate Similarity	NPC185276
0.8061	Intermediate Similarity	NPC212932
0.8061	Intermediate Similarity	NPC293053
0.8061	Intermediate Similarity	NPC107177
0.8061	Intermediate Similarity	NPC149026
0.8061	Intermediate Similarity	NPC18585
0.8061	Intermediate Similarity	NPC278249
0.8061	Intermediate Similarity	NPC310130
0.8061	Intermediate Similarity	NPC91560
0.8061	Intermediate Similarity	NPC164980
0.8061	Intermediate Similarity	NPC68104
0.8061	Intermediate Similarity	NPC190637
0.8061	Intermediate Similarity	NPC125894
0.8061	Intermediate Similarity	NPC166138
0.8061	Intermediate Similarity	NPC106985
0.8061	Intermediate Similarity	NPC478086
0.8061	Intermediate Similarity	NPC214166
0.8061	Intermediate Similarity	NPC169591
0.8061	Intermediate Similarity	NPC81697
0.8061	Intermediate Similarity	NPC39329
0.8061	Intermediate Similarity	NPC24821
0.8061	Intermediate Similarity	NPC11700
0.8061	Intermediate Similarity	NPC143896
0.8061	Intermediate Similarity	NPC175504
0.8061	Intermediate Similarity	NPC77794
0.8061	Intermediate Similarity	NPC221432
0.8061	Intermediate Similarity	NPC75049
0.8061	Intermediate Similarity	NPC316816
0.8049	Intermediate Similarity	NPC156190
0.8049	Intermediate Similarity	NPC96408
0.8049	Intermediate Similarity	NPC324386
0.8049	Intermediate Similarity	NPC166689
0.8049	Intermediate Similarity	NPC279650
0.8049	Intermediate Similarity	NPC4743
0.8049	Intermediate Similarity	NPC312391
0.8049	Intermediate Similarity	NPC17170
0.8049	Intermediate Similarity	NPC213322
0.8049	Intermediate Similarity	NPC110038
0.8049	Intermediate Similarity	NPC103362
0.8049	Intermediate Similarity	NPC258630
0.8049	Intermediate Similarity	NPC3188
0.8049	Intermediate Similarity	NPC248372
0.8024	Intermediate Similarity	NPC166757
0.8024	Intermediate Similarity	NPC14001
0.8024	Intermediate Similarity	NPC201731
0.8024	Intermediate Similarity	NPC24673
0.8024	Intermediate Similarity	NPC79469
0.8024	Intermediate Similarity	NPC97716
0.8024	Intermediate Similarity	NPC140120
0.8024	Intermediate Similarity	NPC104406
0.8024	Intermediate Similarity	NPC237635
0.8012	Intermediate Similarity	NPC473015
0.8012	Intermediate Similarity	NPC271288
0.8012	Intermediate Similarity	NPC197252
0.8012	Intermediate Similarity	NPC470136
0.8012	Intermediate Similarity	NPC236766
0.8012	Intermediate Similarity	NPC39045
0.8012	Intermediate Similarity	NPC131579
0.8012	Intermediate Similarity	NPC326500
0.8012	Intermediate Similarity	NPC470135
0.8012	Intermediate Similarity	NPC473013
0.8012	Intermediate Similarity	NPC235217
0.8012	Intermediate Similarity	NPC473014
0.8012	Intermediate Similarity	NPC273538
0.8012	Intermediate Similarity	NPC216538
0.8012	Intermediate Similarity	NPC278175
0.8012	Intermediate Similarity	NPC257236
0.8012	Intermediate Similarity	NPC234629
0.8012	Intermediate Similarity	NPC311741
0.8012	Intermediate Similarity	NPC131568
0.8012	Intermediate Similarity	NPC209040
0.8011	Intermediate Similarity	NPC204580
0.8	Intermediate Similarity	NPC36181
0.8	Intermediate Similarity	NPC313112
0.8	Intermediate Similarity	NPC266725
0.8	Intermediate Similarity	NPC473042

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 NPC327005 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	734
0.2-0.3	1055
0.3-0.4	1980
0.4-0.5	2592
0.5-0.6	1851
0.6-0.7	614
0.7-0.8	87
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8671	High Similarity	NPD4419	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD4360	Phase 2
0.8197	Intermediate Similarity	NPD4363	Phase 3
0.8171	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD4361	Phase 2
0.8012	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD3446	Phase 1
0.7884	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7584	Approved
0.7821	Intermediate Similarity	NPD6020	Phase 2
0.7805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6585	Discontinued
0.7758	Intermediate Similarity	NPD1549	Phase 2
0.7733	Intermediate Similarity	NPD5890	Approved
0.7733	Intermediate Similarity	NPD7411	Suspended
0.7733	Intermediate Similarity	NPD5889	Approved
0.7711	Intermediate Similarity	NPD2654	Approved
0.7701	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4380	Phase 2
0.7644	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD5006	Approved
0.7617	Intermediate Similarity	NPD5005	Approved
0.7586	Intermediate Similarity	NPD6844	Discontinued
0.7581	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1510	Phase 2
0.7552	Intermediate Similarity	NPD7810	Phase 3
0.7552	Intermediate Similarity	NPD7811	Phase 3
0.7546	Intermediate Similarity	NPD1240	Approved
0.7541	Intermediate Similarity	NPD3823	Discontinued
0.753	Intermediate Similarity	NPD2796	Approved
0.7529	Intermediate Similarity	NPD7212	Phase 2
0.7529	Intermediate Similarity	NPD7213	Phase 3
0.7514	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7075	Discontinued
0.7486	Intermediate Similarity	NPD7577	Discontinued
0.7485	Intermediate Similarity	NPD7447	Phase 1
0.7455	Intermediate Similarity	NPD1607	Approved
0.7443	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7819	Suspended
0.7427	Intermediate Similarity	NPD1511	Approved
0.7424	Intermediate Similarity	NPD7585	Approved
0.7416	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD4420	Approved
0.7386	Intermediate Similarity	NPD6801	Discontinued
0.7386	Intermediate Similarity	NPD1934	Approved
0.7385	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8053	Approved
0.738	Intermediate Similarity	NPD8054	Approved
0.7374	Intermediate Similarity	NPD7583	Approved
0.7363	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3750	Approved
0.7353	Intermediate Similarity	NPD6198	Phase 1
0.7348	Intermediate Similarity	NPD5710	Approved
0.7348	Intermediate Similarity	NPD5711	Approved
0.7345	Intermediate Similarity	NPD2801	Approved
0.7341	Intermediate Similarity	NPD1512	Approved
0.7337	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3140	Approved
0.7333	Intermediate Similarity	NPD3142	Approved
0.7312	Intermediate Similarity	NPD6104	Discontinued
0.7293	Intermediate Similarity	NPD6959	Discontinued
0.7283	Intermediate Similarity	NPD7177	Discontinued
0.7282	Intermediate Similarity	NPD6874	Approved
0.7268	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6666	Approved
0.7267	Intermediate Similarity	NPD6667	Approved
0.7263	Intermediate Similarity	NPD7768	Phase 2
0.7263	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2899	Discontinued
0.7225	Intermediate Similarity	NPD6799	Approved
0.7222	Intermediate Similarity	NPD3749	Approved
0.7216	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5242	Approved
0.7208	Intermediate Similarity	NPD3450	Approved
0.7208	Intermediate Similarity	NPD2493	Approved
0.7208	Intermediate Similarity	NPD3452	Approved
0.7208	Intermediate Similarity	NPD2494	Approved
0.72	Intermediate Similarity	NPD7427	Discontinued
0.7193	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2800	Approved
0.7189	Intermediate Similarity	NPD8099	Discontinued
0.7189	Intermediate Similarity	NPD8252	Approved
0.7189	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8251	Approved
0.7188	Intermediate Similarity	NPD2488	Approved
0.7188	Intermediate Similarity	NPD2490	Approved
0.7179	Intermediate Similarity	NPD2973	Approved
0.7179	Intermediate Similarity	NPD2975	Approved
0.7179	Intermediate Similarity	NPD2974	Approved
0.7175	Intermediate Similarity	NPD6502	Phase 2
0.7174	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6166	Phase 2
0.7164	Intermediate Similarity	NPD7701	Phase 2
0.7163	Intermediate Similarity	NPD7907	Approved
0.7151	Intermediate Similarity	NPD8156	Discontinued
0.715	Intermediate Similarity	NPD3819	Phase 2
0.7143	Intermediate Similarity	NPD4078	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1670	Discontinued
0.71	Intermediate Similarity	NPD4583	Approved
0.71	Intermediate Similarity	NPD4582	Approved
0.71	Intermediate Similarity	NPD3298	Approved
0.7093	Intermediate Similarity	NPD1243	Approved
0.709	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6862	Phase 2
0.7085	Intermediate Similarity	NPD3057	Approved
0.7081	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6599	Discontinued
0.7072	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6788	Approved
0.7072	Intermediate Similarity	NPD3882	Suspended
0.7071	Intermediate Similarity	NPD4580	Approved
0.7067	Intermediate Similarity	NPD4665	Approved
0.7067	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD7054	Approved
0.7056	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2968	Approved
0.7053	Intermediate Similarity	NPD2971	Approved
0.705	Intermediate Similarity	NPD4004	Approved
0.705	Intermediate Similarity	NPD4002	Approved
0.7049	Intermediate Similarity	NPD5494	Approved
0.7049	Intermediate Similarity	NPD2904	Discontinued
0.7041	Intermediate Similarity	NPD6651	Approved
0.7039	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4466	Phase 1
0.7021	Intermediate Similarity	NPD7074	Phase 3
0.7021	Intermediate Similarity	NPD7472	Approved
0.7021	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8285	Discontinued
0.7017	Intermediate Similarity	NPD3817	Phase 2
0.7017	Intermediate Similarity	NPD7318	Phase 3
0.7017	Intermediate Similarity	NPD5977	Approved
0.7017	Intermediate Similarity	NPD5978	Approved
0.701	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD3448	Approved
0.7	Intermediate Similarity	NPD3533	Approved
0.7	Intermediate Similarity	NPD2200	Suspended
0.7	Intermediate Similarity	NPD2972	Approved
0.7	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2491	Approved
0.699	Remote Similarity	NPD4377	Discontinued
0.6989	Remote Similarity	NPD4661	Approved
0.6989	Remote Similarity	NPD4662	Approved
0.6984	Remote Similarity	NPD6797	Phase 2
0.6978	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5183	Approved
0.6973	Remote Similarity	NPD5186	Approved
0.6972	Remote Similarity	NPD7048	Phase 3
0.6971	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2799	Discontinued
0.6959	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7251	Discontinued
0.6944	Remote Similarity	NPD6386	Approved
0.6944	Remote Similarity	NPD6385	Approved
0.694	Remote Similarity	NPD955	Approved
0.6935	Remote Similarity	NPD3297	Approved
0.6932	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8461	Discontinued
0.6923	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4477	Approved
0.6919	Remote Similarity	NPD2935	Discontinued
0.6919	Remote Similarity	NPD4476	Approved
0.6919	Remote Similarity	NPD1551	Phase 2
0.6915	Remote Similarity	NPD3818	Discontinued
0.6911	Remote Similarity	NPD7808	Phase 3
0.6911	Remote Similarity	NPD7549	Discontinued
0.691	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.691	Remote Similarity	NPD920	Approved
0.6907	Remote Similarity	NPD7291	Discontinued
0.6906	Remote Similarity	NPD7317	Phase 3
0.6905	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2313	Discontinued
0.6905	Remote Similarity	NPD5496	Approved
0.69	Remote Similarity	NPD5457	Discontinued
0.69	Remote Similarity	NPD6779	Approved
0.69	Remote Similarity	NPD6781	Approved
0.69	Remote Similarity	NPD6778	Approved
0.69	Remote Similarity	NPD4107	Approved
0.69	Remote Similarity	NPD6782	Approved
0.69	Remote Similarity	NPD6776	Approved
0.69	Remote Similarity	NPD6780	Approved
0.69	Remote Similarity	NPD6777	Approved
0.6898	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2898	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