NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	278.965
LogP:	2.922
LogD:	2.914
LogS:	-3.904
# Rotatable Bonds:	2
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.882
Synthetic Accessibility Score:	2.326
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.765
MDCK Permeability:	1.5176626220636535e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.091
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	95.93152618408203%
Volume Distribution (VD):	0.667
Pgp-substrate:	2.9212327003479004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.548
CYP2C19-substrate:	0.259
CYP2C9-inhibitor:	0.347
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.585
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.614
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	8.854
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.689
Skin Sensitization:	0.72
Carcinogencity:	0.071
Eye Corrosion:	0.004
Eye Irritation:	0.608
Respiratory Toxicity:	0.28

Download Data

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

Natural Product: NPC200557

Natural Product ID:	NPC200557
*Common Name:**	Flavanthridin
IUPAC Name:	5,7-dimethoxy-9,10-dihydrophenanthrene-2,6-diol
Synonyms:	Flavanthridin
Standard InCHIKey:	SOHTUOALNFQEMJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-19-13-8-10-4-3-9-7-11(17)5-6-12(9)14(10)16(20-2)15(13)18/h5-8,17-18H,3-4H2,1-2H3
SMILES:	COc1cc2CCc3cc(ccc3-c2c(c1O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1082453
PubChem CID:	14777891
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16268553]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[16724831]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715978]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[20141173]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407005]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15662	Ligustrum ovalifolium	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4581	Ungernia victoris	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15280	Sideritis grandiflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1575	Mikania luetzelburgii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6178	Solanum euacanthum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13053	Corydalis conspersa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO326	Pittosporum brevicalyx	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	7
MIC	9
Others	8

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	8
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	34100.0	nM	PMID[456011]
NPT1970	Cell Line	THP-1	Homo sapiens	FC	=	1.4	n.a.	PMID[456012]
NPT1970	Cell Line	THP-1	Homo sapiens	FC	=	1.3	n.a.	PMID[456012]
NPT1970	Cell Line	THP-1	Homo sapiens	FC	=	1.2	n.a.	PMID[456012]
NPT1970	Cell Line	THP-1	Homo sapiens	Inhibition	=	8.0	%	PMID[456012]
NPT1970	Cell Line	THP-1	Homo sapiens	Inhibition	=	17.5	%	PMID[456012]
NPT1970	Cell Line	THP-1	Homo sapiens	Inhibition	=	47.0	%	PMID[456012]
NPT1970	Cell Line	THP-1	Homo sapiens	Inhibition	=	64.0	%	PMID[456012]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11.72	ug.mL-1	PMID[456012]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11.66	ug.mL-1	PMID[456012]
NPT1	Others	Radical scavenging activity		IC50	=	10.28	ug.mL-1	PMID[456012]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[456013]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	400000.0	nM	PMID[456013]
NPT610	Others	Molecular identity unknown		MIC	>	400000.0	nM	PMID[456013]

☑ 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 NPC200557 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	454
0.1-0.2	1821
0.2-0.3	4870
0.3-0.4	12662
0.4-0.5	5112
0.5-0.6	3807
0.6-0.7	7120
0.7-0.8	5296
0.8-0.85	836
0.85-0.9	439
0.9-0.95	229
0.95-1	51

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC108198
1.0	High Similarity	NPC158142
1.0	High Similarity	NPC69029
1.0	High Similarity	NPC294884
1.0	High Similarity	NPC10314
0.9922	High Similarity	NPC125649
0.9922	High Similarity	NPC202846
0.9922	High Similarity	NPC143139
0.9846	High Similarity	NPC56329
0.9846	High Similarity	NPC242715
0.9845	High Similarity	NPC313081
0.9845	High Similarity	NPC241241
0.9771	High Similarity	NPC220344
0.9771	High Similarity	NPC275061
0.9771	High Similarity	NPC132804
0.9771	High Similarity	NPC243996
0.9771	High Similarity	NPC79622
0.9771	High Similarity	NPC29868
0.9771	High Similarity	NPC212942
0.9769	High Similarity	NPC30632
0.9767	High Similarity	NPC160697
0.9697	High Similarity	NPC12668
0.9697	High Similarity	NPC308768
0.9695	High Similarity	NPC230919
0.9695	High Similarity	NPC266453
0.9695	High Similarity	NPC200935
0.9695	High Similarity	NPC22902
0.9621	High Similarity	NPC184613
0.9621	High Similarity	NPC105847
0.9621	High Similarity	NPC243759
0.9621	High Similarity	NPC218131
0.9618	High Similarity	NPC205442
0.9615	High Similarity	NPC209199
0.9612	High Similarity	NPC161958
0.9612	High Similarity	NPC14224
0.9609	High Similarity	NPC126836
0.9552	High Similarity	NPC183709
0.9552	High Similarity	NPC175838
0.9545	High Similarity	NPC151656
0.9545	High Similarity	NPC266006
0.9538	High Similarity	NPC32778
0.9474	High Similarity	NPC114171
0.9474	High Similarity	NPC230124
0.9474	High Similarity	NPC6300
0.9453	High Similarity	NPC154866
0.9403	High Similarity	NPC165026
0.9403	High Similarity	NPC295719
0.9403	High Similarity	NPC34431
0.9403	High Similarity	NPC73505
0.9398	High Similarity	NPC201145
0.9398	High Similarity	NPC73535
0.9398	High Similarity	NPC25111
0.9398	High Similarity	NPC90615
0.9398	High Similarity	NPC272157
0.9398	High Similarity	NPC6262
0.9385	High Similarity	NPC15543
0.9375	High Similarity	NPC124452
0.9375	High Similarity	NPC82679
0.9375	High Similarity	NPC236791
0.9375	High Similarity	NPC282000
0.9375	High Similarity	NPC324112
0.9375	High Similarity	NPC159968
0.9375	High Similarity	NPC74817
0.9375	High Similarity	NPC169474
0.9375	High Similarity	NPC266555
0.9375	High Similarity	NPC471986
0.9375	High Similarity	NPC293054
0.9375	High Similarity	NPC246620
0.9333	High Similarity	NPC472089
0.9323	High Similarity	NPC300846
0.9323	High Similarity	NPC476639
0.9323	High Similarity	NPC114155
0.9318	High Similarity	NPC7515
0.9318	High Similarity	NPC289258
0.9318	High Similarity	NPC276026
0.9318	High Similarity	NPC206737
0.9318	High Similarity	NPC56764
0.9318	High Similarity	NPC469659
0.9318	High Similarity	NPC188378
0.9318	High Similarity	NPC555
0.9313	High Similarity	NPC228843
0.9302	High Similarity	NPC28765
0.9297	High Similarity	NPC223136
0.9297	High Similarity	NPC170485
0.9297	High Similarity	NPC44748
0.9297	High Similarity	NPC18924
0.9297	High Similarity	NPC103823
0.9297	High Similarity	NPC28730
0.9297	High Similarity	NPC214406
0.9297	High Similarity	NPC78974
0.9297	High Similarity	NPC223953
0.9265	High Similarity	NPC191231
0.9265	High Similarity	NPC472088
0.9265	High Similarity	NPC472087
0.9259	High Similarity	NPC472090
0.9259	High Similarity	NPC472091
0.9259	High Similarity	NPC472092
0.9248	High Similarity	NPC261873
0.9248	High Similarity	NPC240279
0.9248	High Similarity	NPC111655
0.9248	High Similarity	NPC180602
0.9248	High Similarity	NPC256262
0.9248	High Similarity	NPC214853
0.9248	High Similarity	NPC55239
0.9248	High Similarity	NPC283009
0.9237	High Similarity	NPC149337
0.9237	High Similarity	NPC471983
0.9225	High Similarity	NPC127587
0.9225	High Similarity	NPC252131
0.9225	High Similarity	NPC236760
0.9219	High Similarity	NPC299584
0.9219	High Similarity	NPC298757
0.9219	High Similarity	NPC57490
0.9219	High Similarity	NPC251855
0.9219	High Similarity	NPC116907
0.9219	High Similarity	NPC221077
0.9219	High Similarity	NPC265483
0.9219	High Similarity	NPC472093
0.9219	High Similarity	NPC117214
0.9219	High Similarity	NPC105925
0.9219	High Similarity	NPC60885
0.9219	High Similarity	NPC82483
0.9219	High Similarity	NPC475169
0.9219	High Similarity	NPC208950
0.9219	High Similarity	NPC234400
0.9219	High Similarity	NPC233410
0.9219	High Similarity	NPC203133
0.9219	High Similarity	NPC193544
0.9219	High Similarity	NPC17943
0.9209	High Similarity	NPC262297
0.9197	High Similarity	NPC469630
0.9185	High Similarity	NPC55947
0.9179	High Similarity	NPC133025
0.9173	High Similarity	NPC311256
0.9173	High Similarity	NPC103967
0.9167	High Similarity	NPC6451
0.916	High Similarity	NPC234488
0.916	High Similarity	NPC311680
0.916	High Similarity	NPC299221
0.916	High Similarity	NPC51840
0.9147	High Similarity	NPC76451
0.9141	High Similarity	NPC228503
0.9141	High Similarity	NPC5796
0.9141	High Similarity	NPC138248
0.9141	High Similarity	NPC206487
0.9137	High Similarity	NPC126291
0.913	High Similarity	NPC469795
0.9124	High Similarity	NPC470917
0.9111	High Similarity	NPC156948
0.9111	High Similarity	NPC35550
0.9111	High Similarity	NPC46277
0.9111	High Similarity	NPC86605
0.9111	High Similarity	NPC3072
0.9111	High Similarity	NPC301765
0.9091	High Similarity	NPC232275
0.9091	High Similarity	NPC474356
0.9091	High Similarity	NPC282508
0.9091	High Similarity	NPC45715
0.9091	High Similarity	NPC12275
0.9084	High Similarity	NPC58164
0.9084	High Similarity	NPC212015
0.9084	High Similarity	NPC10225
0.9077	High Similarity	NPC21563
0.907	High Similarity	NPC266705
0.907	High Similarity	NPC113495
0.907	High Similarity	NPC105718
0.907	High Similarity	NPC278955
0.907	High Similarity	NPC228771
0.907	High Similarity	NPC29008
0.9062	High Similarity	NPC84086
0.9062	High Similarity	NPC228922
0.9062	High Similarity	NPC282496
0.9062	High Similarity	NPC233526
0.9062	High Similarity	NPC197757
0.9062	High Similarity	NPC95168
0.9062	High Similarity	NPC136319
0.9062	High Similarity	NPC121115
0.9051	High Similarity	NPC265075
0.9044	High Similarity	NPC70682
0.9044	High Similarity	NPC471183
0.9044	High Similarity	NPC260741
0.9044	High Similarity	NPC32630
0.9037	High Similarity	NPC162659
0.9037	High Similarity	NPC270456
0.9037	High Similarity	NPC248727
0.9037	High Similarity	NPC234952
0.9037	High Similarity	NPC265433
0.903	High Similarity	NPC317380
0.9023	High Similarity	NPC86655
0.9023	High Similarity	NPC218884
0.9023	High Similarity	NPC202762
0.9023	High Similarity	NPC127624
0.9015	High Similarity	NPC192687
0.9015	High Similarity	NPC224157
0.9008	High Similarity	NPC206615
0.9008	High Similarity	NPC266691
0.9008	High Similarity	NPC23012
0.9008	High Similarity	NPC215300
0.9008	High Similarity	NPC98631
0.9008	High Similarity	NPC470213

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 NPC200557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	980
0.2-0.3	1683
0.3-0.4	2831
0.4-0.5	1610
0.5-0.6	867
0.6-0.7	627
0.7-0.8	141
0.8-0.85	9
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8939	High Similarity	NPD3027	Phase 3
0.8722	High Similarity	NPD1529	Clinical (unspecified phase)
0.8647	High Similarity	NPD1530	Clinical (unspecified phase)
0.8603	High Similarity	NPD1612	Clinical (unspecified phase)
0.8603	High Similarity	NPD1613	Approved
0.8519	High Similarity	NPD4625	Phase 3
0.8321	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD4908	Phase 1
0.8235	Intermediate Similarity	NPD3018	Phase 2
0.8201	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD3620	Phase 2
0.817	Intermediate Similarity	NPD6234	Discontinued
0.8129	Intermediate Similarity	NPD6232	Discontinued
0.8079	Intermediate Similarity	NPD37	Approved
0.8074	Intermediate Similarity	NPD2982	Phase 2
0.8074	Intermediate Similarity	NPD2983	Phase 2
0.8062	Intermediate Similarity	NPD5283	Phase 1
0.806	Intermediate Similarity	NPD1610	Phase 2
0.8047	Intermediate Similarity	NPD228	Approved
0.8	Intermediate Similarity	NPD2981	Phase 2
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7941	Intermediate Similarity	NPD4749	Approved
0.7941	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD4966	Approved
0.7922	Intermediate Similarity	NPD4967	Phase 2
0.7922	Intermediate Similarity	NPD4965	Approved
0.7899	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1548	Phase 1
0.7843	Intermediate Similarity	NPD1934	Approved
0.7817	Intermediate Similarity	NPD4060	Phase 1
0.7812	Intermediate Similarity	NPD7228	Approved
0.781	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2801	Approved
0.7792	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5844	Phase 1
0.7755	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6674	Discontinued
0.7752	Intermediate Similarity	NPD3021	Approved
0.7752	Intermediate Similarity	NPD3022	Approved
0.7722	Intermediate Similarity	NPD7199	Phase 2
0.7647	Intermediate Similarity	NPD4005	Discontinued
0.7625	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3540	Phase 1
0.7589	Intermediate Similarity	NPD2861	Phase 2
0.7586	Intermediate Similarity	NPD4097	Suspended
0.758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3882	Suspended
0.7578	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6166	Phase 2
0.7578	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1465	Phase 2
0.7551	Intermediate Similarity	NPD3539	Phase 1
0.755	Intermediate Similarity	NPD1511	Approved
0.7536	Intermediate Similarity	NPD3705	Approved
0.7532	Intermediate Similarity	NPD4055	Discovery
0.7518	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8054	Approved
0.7485	Intermediate Similarity	NPD8053	Approved
0.7481	Intermediate Similarity	NPD4750	Phase 3
0.7468	Intermediate Similarity	NPD1653	Approved
0.7451	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1512	Approved
0.7448	Intermediate Similarity	NPD1558	Phase 1
0.7432	Intermediate Similarity	NPD6100	Approved
0.7432	Intermediate Similarity	NPD6099	Approved
0.7417	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5735	Approved
0.7397	Intermediate Similarity	NPD3657	Discovery
0.7394	Intermediate Similarity	NPD4624	Approved
0.7381	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD8651	Approved
0.7368	Intermediate Similarity	NPD7124	Phase 2
0.7351	Intermediate Similarity	NPD3750	Approved
0.7344	Intermediate Similarity	NPD846	Approved
0.7344	Intermediate Similarity	NPD940	Approved
0.7338	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2342	Discontinued
0.7324	Intermediate Similarity	NPD3094	Phase 2
0.732	Intermediate Similarity	NPD4357	Discontinued
0.732	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1651	Approved
0.731	Intermediate Similarity	NPD5110	Phase 2
0.731	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5109	Approved
0.731	Intermediate Similarity	NPD5111	Phase 2
0.7305	Intermediate Similarity	NPD7240	Approved
0.7299	Intermediate Similarity	NPD5536	Phase 2
0.7296	Intermediate Similarity	NPD3817	Phase 2
0.729	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7074	Phase 3
0.7286	Intermediate Similarity	NPD422	Phase 1
0.7286	Intermediate Similarity	NPD3092	Approved
0.7284	Intermediate Similarity	NPD6959	Discontinued
0.7273	Intermediate Similarity	NPD7447	Phase 1
0.7273	Intermediate Similarity	NPD3818	Discontinued
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7266	Intermediate Similarity	NPD1242	Phase 1
0.7261	Intermediate Similarity	NPD4380	Phase 2
0.7254	Intermediate Similarity	NPD1283	Approved
0.7254	Intermediate Similarity	NPD6696	Suspended
0.7248	Intermediate Similarity	NPD1510	Phase 2
0.7241	Intermediate Similarity	NPD7095	Approved
0.7237	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3892	Phase 2
0.7233	Intermediate Similarity	NPD7819	Suspended
0.723	Intermediate Similarity	NPD1607	Approved
0.7229	Intermediate Similarity	NPD7054	Approved
0.7219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5089	Approved
0.7215	Intermediate Similarity	NPD5090	Approved
0.7211	Intermediate Similarity	NPD1240	Approved
0.7208	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7213	Phase 3
0.7208	Intermediate Similarity	NPD7041	Phase 2
0.7208	Intermediate Similarity	NPD7212	Phase 2
0.7205	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5691	Approved
0.719	Intermediate Similarity	NPD5241	Discontinued
0.7186	Intermediate Similarity	NPD7472	Approved
0.7185	Intermediate Similarity	NPD7635	Approved
0.7183	Intermediate Similarity	NPD5327	Phase 3
0.7183	Intermediate Similarity	NPD1669	Approved
0.7181	Intermediate Similarity	NPD6111	Discontinued
0.7171	Intermediate Similarity	NPD5177	Phase 3
0.7171	Intermediate Similarity	NPD3060	Approved
0.7153	Intermediate Similarity	NPD6671	Approved
0.7153	Intermediate Similarity	NPD7157	Approved
0.7153	Intermediate Similarity	NPD709	Approved
0.7153	Intermediate Similarity	NPD6584	Phase 3
0.7152	Intermediate Similarity	NPD2489	Approved
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD4675	Approved
0.7152	Intermediate Similarity	NPD27	Approved
0.7152	Intermediate Similarity	NPD4678	Approved
0.7151	Intermediate Similarity	NPD7906	Approved
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD2684	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3051	Approved
0.7134	Intermediate Similarity	NPD7229	Phase 3
0.7122	Intermediate Similarity	NPD3091	Approved
0.7118	Intermediate Similarity	NPD4577	Approved
0.7118	Intermediate Similarity	NPD4578	Approved
0.7117	Intermediate Similarity	NPD5494	Approved
0.711	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7075	Discontinued
0.7095	Intermediate Similarity	NPD943	Approved
0.7095	Intermediate Similarity	NPD4140	Approved
0.7095	Intermediate Similarity	NPD2238	Phase 2
0.7093	Intermediate Similarity	NPD4663	Approved
0.7091	Intermediate Similarity	NPD2969	Approved
0.7091	Intermediate Similarity	NPD2970	Approved
0.709	Intermediate Similarity	NPD5451	Approved
0.7089	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7081	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2677	Approved
0.7078	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2219	Phase 1
0.7075	Intermediate Similarity	NPD6798	Discontinued
0.7071	Intermediate Similarity	NPD1357	Approved
0.7067	Intermediate Similarity	NPD4536	Approved
0.7067	Intermediate Similarity	NPD4538	Approved
0.7067	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8251	Approved
0.7066	Intermediate Similarity	NPD8099	Discontinued
0.7066	Intermediate Similarity	NPD8252	Approved
0.7059	Intermediate Similarity	NPD7843	Approved
0.7059	Intermediate Similarity	NPD7549	Discontinued
0.7054	Intermediate Similarity	NPD3020	Approved
0.7051	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2532	Approved
0.7051	Intermediate Similarity	NPD2534	Approved
0.7051	Intermediate Similarity	NPD2533	Approved
0.7051	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5124	Phase 1
0.7042	Intermediate Similarity	NPD1281	Approved
0.7042	Intermediate Similarity	NPD1611	Approved
0.7042	Intermediate Similarity	NPD1091	Approved
0.7041	Intermediate Similarity	NPD6797	Phase 2
0.7041	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6788	Approved
0.703	Intermediate Similarity	NPD3787	Discontinued
0.7024	Intermediate Similarity	NPD8156	Discontinued
0.7021	Intermediate Similarity	NPD6516	Phase 2
0.7021	Intermediate Similarity	NPD5846	Approved
0.702	Intermediate Similarity	NPD4108	Discontinued
0.702	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3748	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