NPASS Compound

Structure

NPC470676 OpenBabel07101718182D 25 28 0 0 1 0 0 0 0 0999 V2000 -5.0037 2.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1698 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3096 2.2287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2118 2.9123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7833 0.3199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0037 1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4887 0.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1246 0.2627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1698 1.4444 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.9259 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5441 1.4210 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5019 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5019 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3358 1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6065 2.0339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 0.4815 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3358 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3358 2.8889 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 -1.1683 2.2863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 21 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 23 2 0 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	362.161
LogP:	5.734
LogD:	4.723
LogS:	-3.101
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.798
Synthetic Accessibility Score:	5.099
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.671
MDCK Permeability:	1.7099770047934726e-05
Pgp-inhibitor:	0.472
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	100.06341552734375%
Volume Distribution (VD):	2.339
Pgp-substrate:	1.360136866569519%

ADMET: Metabolism

CYP1A2-inhibitor:	0.297
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.423
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.548
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.582
CYP2D6-substrate:	0.224
CYP3A4-inhibitor:	0.571
CYP3A4-substrate:	0.833

ADMET: Excretion

Clearance (CL):	3.393
Half-life (T1/2):	0.055

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.736
Drug-inuced Liver Injury (DILI):	0.548
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.458
Maximum Recommended Daily Dose:	0.817
Skin Sensitization:	0.118
Carcinogencity:	0.357
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.854

Download Data

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

Natural Product: NPC470676

Natural Product ID:	NPC470676
*Common Name:**	Empetrifranzinan C
IUPAC Name:	n.a.
Synonyms:	Empetrifranzinan C
Standard InCHIKey:	FUOLYAMVOGPERE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H28O4/c1-6-11(2)18(23)17-14(22)9-15-16-12-10-21(5,24-15)8-7-13(12)20(3,4)25-19(16)17/h9,11-13,22H,6-8,10H2,1-5H3
SMILES:	CCC(C)C(=O)C1=C2C3=C(C=C1O)OC4(CCC(C3C4)C(O2)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152500
PubChem CID:	71449450
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO33078	hypericum empetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23030826]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24930002]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26358281]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[8862040]

☑ 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	1
IC50	1
MIC	3
Others	4

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	45000.0	nM	PMID[513898]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	20.0	%	PMID[513898]
NPT306	Cell Line	PC-3	Homo sapiens	GI	<	20.0	%	PMID[513898]
NPT139	Cell Line	HT-29	Homo sapiens	GI	=	20.0	%	PMID[513898]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9200.0	nM	PMID[513897]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	45000.0	nM	PMID[513898]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	1.0	ug.mL-1	PMID[513898]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	1.0	ug.mL-1	PMID[513898]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	1.0	ug.mL-1	PMID[513898]

☑ 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 NPC470676 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	395
0.1-0.2	1627
0.2-0.3	3528
0.3-0.4	8802
0.4-0.5	9932
0.5-0.6	3898
0.6-0.7	5669
0.7-0.8	5665
0.8-0.85	2093
0.85-0.9	994
0.9-0.95	85
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473135
1.0	High Similarity	NPC473132
0.9645	High Similarity	NPC470673
0.9645	High Similarity	NPC470674
0.9645	High Similarity	NPC117716
0.964	High Similarity	NPC469818
0.9384	High Similarity	NPC305965
0.9379	High Similarity	NPC473016
0.9362	High Similarity	NPC477272
0.9357	High Similarity	NPC470672
0.9357	High Similarity	NPC474487
0.9357	High Similarity	NPC470671
0.9357	High Similarity	NPC474504
0.9306	High Similarity	NPC477955
0.9301	High Similarity	NPC219915
0.9252	High Similarity	NPC473131
0.9252	High Similarity	NPC470675
0.9236	High Similarity	NPC271288
0.9231	High Similarity	NPC144499
0.92	High Similarity	NPC272196
0.9189	High Similarity	NPC87708
0.9184	High Similarity	NPC29777
0.9184	High Similarity	NPC471115
0.9184	High Similarity	NPC150928
0.9167	High Similarity	NPC166138
0.9167	High Similarity	NPC38219
0.9167	High Similarity	NPC106985
0.9167	High Similarity	NPC18585
0.9139	High Similarity	NPC472617
0.9133	High Similarity	NPC4547
0.9128	High Similarity	NPC95842
0.9128	High Similarity	NPC329844
0.9128	High Similarity	NPC178964
0.9128	High Similarity	NPC280530
0.9122	High Similarity	NPC232645
0.9122	High Similarity	NPC478148
0.9122	High Similarity	NPC474417
0.9122	High Similarity	NPC149526
0.9122	High Similarity	NPC72958
0.9116	High Similarity	NPC10027
0.9116	High Similarity	NPC65589
0.9116	High Similarity	NPC288036
0.9116	High Similarity	NPC97029
0.9116	High Similarity	NPC473978
0.9116	High Similarity	NPC158338
0.9116	High Similarity	NPC100985
0.9116	High Similarity	NPC97028
0.9116	High Similarity	NPC65775
0.911	High Similarity	NPC296998
0.911	High Similarity	NPC308200
0.911	High Similarity	NPC473077
0.9103	High Similarity	NPC131568
0.9103	High Similarity	NPC131579
0.9097	High Similarity	NPC59739
0.9097	High Similarity	NPC62840
0.9097	High Similarity	NPC310340
0.9097	High Similarity	NPC293852
0.9097	High Similarity	NPC299080
0.9097	High Similarity	NPC214236
0.9097	High Similarity	NPC217083
0.9097	High Similarity	NPC78803
0.9091	High Similarity	NPC69769
0.9091	High Similarity	NPC275734
0.9085	High Similarity	NPC470669
0.9085	High Similarity	NPC131130
0.9085	High Similarity	NPC473022
0.9085	High Similarity	NPC470668
0.9079	High Similarity	NPC472618
0.9067	High Similarity	NPC166054
0.9067	High Similarity	NPC275575
0.9067	High Similarity	NPC55662
0.906	High Similarity	NPC217447
0.906	High Similarity	NPC142527
0.9054	High Similarity	NPC472633
0.9054	High Similarity	NPC158866
0.9054	High Similarity	NPC227122
0.9048	High Similarity	NPC256672
0.9048	High Similarity	NPC145467
0.9048	High Similarity	NPC296869
0.9048	High Similarity	NPC27221
0.9048	High Similarity	NPC39195
0.9048	High Similarity	NPC7025
0.9041	High Similarity	NPC20488
0.9041	High Similarity	NPC187282
0.9041	High Similarity	NPC83357
0.9041	High Similarity	NPC267375
0.9041	High Similarity	NPC111786
0.9041	High Similarity	NPC88964
0.9041	High Similarity	NPC285630
0.9041	High Similarity	NPC301276
0.9041	High Similarity	NPC195621
0.9041	High Similarity	NPC214774
0.9041	High Similarity	NPC54577
0.9041	High Similarity	NPC127059
0.9041	High Similarity	NPC196114
0.9041	High Similarity	NPC475052
0.9041	High Similarity	NPC67805
0.9041	High Similarity	NPC470647
0.9041	High Similarity	NPC312973
0.9041	High Similarity	NPC290133
0.9041	High Similarity	NPC176229
0.9041	High Similarity	NPC246948
0.9041	High Similarity	NPC142405
0.9041	High Similarity	NPC24136
0.9034	High Similarity	NPC81697
0.9034	High Similarity	NPC223812
0.9034	High Similarity	NPC214166
0.9034	High Similarity	NPC85162
0.9034	High Similarity	NPC11700
0.9034	High Similarity	NPC316816
0.9034	High Similarity	NPC125894
0.9034	High Similarity	NPC278249
0.9034	High Similarity	NPC107177
0.9034	High Similarity	NPC77794
0.9034	High Similarity	NPC478086
0.9028	High Similarity	NPC282300
0.9028	High Similarity	NPC205006
0.9028	High Similarity	NPC156590
0.9028	High Similarity	NPC96408
0.9028	High Similarity	NPC147688
0.9028	High Similarity	NPC156190
0.9028	High Similarity	NPC17170
0.9028	High Similarity	NPC166689
0.9028	High Similarity	NPC40118
0.9028	High Similarity	NPC64908
0.9028	High Similarity	NPC126534
0.9028	High Similarity	NPC118840
0.9028	High Similarity	NPC279650
0.9028	High Similarity	NPC232021
0.9028	High Similarity	NPC258630
0.9021	High Similarity	NPC55018
0.9021	High Similarity	NPC96565
0.9021	High Similarity	NPC216978
0.9021	High Similarity	NPC220062
0.9021	High Similarity	NPC301217
0.9021	High Similarity	NPC303633
0.9013	High Similarity	NPC474373
0.9007	High Similarity	NPC164427
0.9	High Similarity	NPC210942
0.9	High Similarity	NPC169990
0.9	High Similarity	NPC472799
0.8993	High Similarity	NPC474023
0.8993	High Similarity	NPC312549
0.8993	High Similarity	NPC178484
0.8993	High Similarity	NPC209142
0.8993	High Similarity	NPC474021
0.8986	High Similarity	NPC329933
0.8986	High Similarity	NPC471114
0.898	High Similarity	NPC166757
0.898	High Similarity	NPC110303
0.898	High Similarity	NPC79469
0.898	High Similarity	NPC34802
0.898	High Similarity	NPC104406
0.898	High Similarity	NPC24673
0.898	High Similarity	NPC23728
0.898	High Similarity	NPC97716
0.898	High Similarity	NPC7943
0.898	High Similarity	NPC14001
0.898	High Similarity	NPC140120
0.898	High Similarity	NPC237635
0.898	High Similarity	NPC123202
0.898	High Similarity	NPC283234
0.898	High Similarity	NPC201731
0.898	High Similarity	NPC10990
0.898	High Similarity	NPC300988
0.898	High Similarity	NPC22005
0.8973	High Similarity	NPC470890
0.8973	High Similarity	NPC326500
0.8973	High Similarity	NPC473015
0.8973	High Similarity	NPC311144
0.8973	High Similarity	NPC209040
0.8973	High Similarity	NPC234629
0.8973	High Similarity	NPC235217
0.8973	High Similarity	NPC473013
0.8973	High Similarity	NPC311741
0.8973	High Similarity	NPC473014
0.8966	High Similarity	NPC265040
0.8966	High Similarity	NPC37496
0.8966	High Similarity	NPC226636
0.8966	High Similarity	NPC148757
0.8966	High Similarity	NPC1089
0.8966	High Similarity	NPC296917
0.8966	High Similarity	NPC324134
0.8966	High Similarity	NPC10937
0.8966	High Similarity	NPC76338
0.8966	High Similarity	NPC177354
0.8966	High Similarity	NPC76372
0.8966	High Similarity	NPC306829
0.8966	High Similarity	NPC64915
0.8966	High Similarity	NPC161506
0.8966	High Similarity	NPC125855
0.8966	High Similarity	NPC297600
0.8966	High Similarity	NPC167624
0.8966	High Similarity	NPC78
0.8966	High Similarity	NPC227579
0.8966	High Similarity	NPC194432
0.8966	High Similarity	NPC107572
0.8966	High Similarity	NPC220998
0.8966	High Similarity	NPC223500
0.8966	High Similarity	NPC11561

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 NPC470676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	970
0.2-0.3	1602
0.3-0.4	2612
0.4-0.5	1956
0.5-0.6	1058
0.6-0.7	414
0.7-0.8	143
0.8-0.85	26
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8896	High Similarity	NPD6959	Discontinued
0.8844	High Similarity	NPD4378	Clinical (unspecified phase)
0.8844	High Similarity	NPD7410	Clinical (unspecified phase)
0.8816	High Similarity	NPD8443	Clinical (unspecified phase)
0.8627	High Similarity	NPD7819	Suspended
0.8627	High Similarity	NPD2393	Clinical (unspecified phase)
0.8621	High Similarity	NPD1552	Clinical (unspecified phase)
0.8621	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1549	Phase 2
0.8552	High Similarity	NPD6099	Approved
0.8552	High Similarity	NPD6100	Approved
0.8503	High Similarity	NPD2800	Approved
0.8497	Intermediate Similarity	NPD7411	Suspended
0.8435	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD4380	Phase 2
0.8356	Intermediate Similarity	NPD1510	Phase 2
0.8345	Intermediate Similarity	NPD1607	Approved
0.8344	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD1240	Approved
0.8323	Intermediate Similarity	NPD1934	Approved
0.8322	Intermediate Similarity	NPD3750	Approved
0.8299	Intermediate Similarity	NPD2796	Approved
0.8278	Intermediate Similarity	NPD1511	Approved
0.8269	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD5494	Approved
0.8224	Intermediate Similarity	NPD2534	Approved
0.8224	Intermediate Similarity	NPD2533	Approved
0.8224	Intermediate Similarity	NPD2532	Approved
0.8219	Intermediate Similarity	NPD6651	Approved
0.82	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1512	Approved
0.8165	Intermediate Similarity	NPD7768	Phase 2
0.8153	Intermediate Similarity	NPD2801	Approved
0.8148	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6166	Phase 2
0.8148	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7473	Discontinued
0.8089	Intermediate Similarity	NPD6801	Discontinued
0.8039	Intermediate Similarity	NPD7390	Discontinued
0.8025	Intermediate Similarity	NPD6232	Discontinued
0.7987	Intermediate Similarity	NPD3748	Approved
0.7987	Intermediate Similarity	NPD2799	Discontinued
0.7962	Intermediate Similarity	NPD6599	Discontinued
0.7952	Intermediate Similarity	NPD7074	Phase 3
0.7945	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3882	Suspended
0.7925	Intermediate Similarity	NPD1465	Phase 2
0.7922	Intermediate Similarity	NPD6799	Approved
0.7898	Intermediate Similarity	NPD3226	Approved
0.7895	Intermediate Similarity	NPD1243	Approved
0.7895	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD7054	Approved
0.7881	Intermediate Similarity	NPD2346	Discontinued
0.7877	Intermediate Similarity	NPD4625	Phase 3
0.7844	Intermediate Similarity	NPD7472	Approved
0.7832	Intermediate Similarity	NPD4749	Approved
0.7826	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1551	Phase 2
0.7815	Intermediate Similarity	NPD2935	Discontinued
0.7811	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD4908	Phase 1
0.7798	Intermediate Similarity	NPD6797	Phase 2
0.7764	Intermediate Similarity	NPD3817	Phase 2
0.7763	Intermediate Similarity	NPD2344	Approved
0.7751	Intermediate Similarity	NPD6559	Discontinued
0.7751	Intermediate Similarity	NPD7251	Discontinued
0.7706	Intermediate Similarity	NPD7808	Phase 3
0.7703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5710	Approved
0.7697	Intermediate Similarity	NPD5711	Approved
0.7658	Intermediate Similarity	NPD920	Approved
0.7619	Intermediate Similarity	NPD3818	Discontinued
0.7588	Intermediate Similarity	NPD5953	Discontinued
0.7584	Intermediate Similarity	NPD2313	Discontinued
0.7584	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3268	Approved
0.7574	Intermediate Similarity	NPD7286	Phase 2
0.7571	Intermediate Similarity	NPD4360	Phase 2
0.7571	Intermediate Similarity	NPD4363	Phase 3
0.7569	Intermediate Similarity	NPD1610	Phase 2
0.7564	Intermediate Similarity	NPD2309	Approved
0.7562	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2798	Approved
0.755	Intermediate Similarity	NPD5124	Phase 1
0.755	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5403	Approved
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD943	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7483	Intermediate Similarity	NPD2797	Approved
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7458	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7448	Intermediate Similarity	NPD1201	Approved
0.7439	Intermediate Similarity	NPD5402	Approved
0.7421	Intermediate Similarity	NPD5401	Approved
0.7421	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4308	Phase 3
0.7397	Intermediate Similarity	NPD9717	Approved
0.7397	Intermediate Similarity	NPD1608	Approved
0.7389	Intermediate Similarity	NPD7003	Approved
0.7365	Intermediate Similarity	NPD1470	Approved
0.7346	Intermediate Similarity	NPD7458	Discontinued
0.7345	Intermediate Similarity	NPD4287	Approved
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4361	Phase 2
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7329	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2654	Approved
0.7308	Intermediate Similarity	NPD1471	Phase 3
0.7305	Intermediate Similarity	NPD919	Approved
0.7294	Intermediate Similarity	NPD2403	Approved
0.729	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD5761	Phase 2
0.7273	Intermediate Similarity	NPD5760	Phase 2
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3267	Approved
0.7248	Intermediate Similarity	NPD3266	Approved
0.7237	Intermediate Similarity	NPD411	Approved
0.7237	Intermediate Similarity	NPD3764	Approved
0.7219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6832	Phase 2
0.7219	Intermediate Similarity	NPD1247	Approved
0.7209	Intermediate Similarity	NPD3751	Discontinued
0.7192	Intermediate Similarity	NPD17	Approved
0.7181	Intermediate Similarity	NPD3225	Approved
0.7179	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3787	Discontinued
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
0.7172	Intermediate Similarity	NPD1548	Phase 1
0.7162	Intermediate Similarity	NPD3972	Approved
0.716	Intermediate Similarity	NPD6273	Approved
0.7151	Intermediate Similarity	NPD7697	Approved
0.7151	Intermediate Similarity	NPD7698	Approved
0.7151	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD8151	Discontinued
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7126	Intermediate Similarity	NPD1729	Discontinued
0.7118	Intermediate Similarity	NPD7199	Phase 2
0.7117	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7177	Discontinued
0.711	Intermediate Similarity	NPD7228	Approved
0.7108	Intermediate Similarity	NPD37	Approved
0.7104	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6234	Discontinued
0.7099	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD447	Suspended
0.7097	Intermediate Similarity	NPD230	Phase 1
0.7091	Intermediate Similarity	NPD6585	Discontinued
0.7086	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4967	Phase 2
0.7083	Intermediate Similarity	NPD4965	Approved
0.7083	Intermediate Similarity	NPD4966	Approved
0.7081	Intermediate Similarity	NPD3300	Phase 2
0.7079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7783	Phase 2
0.7067	Intermediate Similarity	NPD6696	Suspended
0.7067	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD7435	Discontinued
0.7056	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6104	Discontinued
0.7039	Intermediate Similarity	NPD2861	Phase 2
0.7037	Intermediate Similarity	NPD7584	Approved
0.7035	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1613	Approved
0.7032	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4060	Phase 1
0.7024	Intermediate Similarity	NPD2296	Approved
0.7021	Intermediate Similarity	NPD7871	Phase 2
0.7021	Intermediate Similarity	NPD7870	Phase 2
0.702	Intermediate Similarity	NPD1164	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