NPASS Compound

Structure

CID212942 OpenBabel06191716002D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 -2.0000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 2.5981 1.5000 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 -0.8660 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 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 0.0000 1.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.1
Volume:	287.755
LogP:	3.022
LogD:	2.866
LogS:	-3.662
# Rotatable Bonds:	2
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	2.623
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:	-4.946
MDCK Permeability:	1.4657228348369244e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	97.03849029541016%
Volume Distribution (VD):	0.547
Pgp-substrate:	3.70833158493042%

ADMET: Metabolism

CYP1A2-inhibitor:	0.86
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.115
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.302
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.239
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	8.205
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.143
AMES Toxicity:	0.641
Rat Oral Acute Toxicity:	0.434
Maximum Recommended Daily Dose:	0.247
Skin Sensitization:	0.774
Carcinogencity:	0.054
Eye Corrosion:	0.004
Eye Irritation:	0.913
Respiratory Toxicity:	0.534

Download Data

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

Natural Product: NPC212942

Natural Product ID:	NPC212942
*Common Name:**	Calanhydroquinone B
IUPAC Name:	5,6-dimethoxy-9,10-dihydrophenanthrene-1,4,7-triol
Synonyms:	Calanhydroquinone B
Standard InCHIKey:	NLKJYEXGUVVXMN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-20-15-12(19)7-8-3-4-9-10(17)5-6-11(18)14(9)13(8)16(15)21-2/h5-7,17-19H,3-4H2,1-2H3
SMILES:	COc1c(cc2CCc3c(ccc(c3-c2c1OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562912
PubChem CID:	25243458
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
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18640035]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193043]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23795939]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5001	Ramalina calicaris	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5822	Suberites massa	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14623	Senecio clevelandi	Species	Asteraceae	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
EC50	7

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	4.07	ug.mL-1	PMID[529662]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	2.62	ug.mL-1	PMID[529662]
NPT90	Cell Line	DU-145	Homo sapiens	EC50	=	5.46	ug.mL-1	PMID[529662]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	5.16	ug.mL-1	PMID[529662]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	3.28	ug.mL-1	PMID[529662]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	3.75	ug.mL-1	PMID[529662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	5.24	ug.mL-1	PMID[529662]

☑ 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 NPC212942 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	476
0.1-0.2	1844
0.2-0.3	4972
0.3-0.4	12675
0.4-0.5	5093
0.5-0.6	3820
0.6-0.7	7272
0.7-0.8	5096
0.8-0.85	779
0.85-0.9	422
0.9-0.95	214
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC79622
1.0	High Similarity	NPC29868
0.9847	High Similarity	NPC205442
0.9847	High Similarity	NPC202846
0.9847	High Similarity	NPC143139
0.9776	High Similarity	NPC175838
0.9771	High Similarity	NPC108198
0.9771	High Similarity	NPC69029
0.9771	High Similarity	NPC294884
0.9771	High Similarity	NPC158142
0.9771	High Similarity	NPC10314
0.9771	High Similarity	NPC200557
0.9695	High Similarity	NPC125649
0.9695	High Similarity	NPC160697
0.9627	High Similarity	NPC73505
0.9627	High Similarity	NPC165026
0.9627	High Similarity	NPC295719
0.9627	High Similarity	NPC12668
0.9627	High Similarity	NPC308768
0.9627	High Similarity	NPC34431
0.9624	High Similarity	NPC201145
0.9624	High Similarity	NPC272157
0.9624	High Similarity	NPC73535
0.9624	High Similarity	NPC6262
0.9624	High Similarity	NPC242715
0.9624	High Similarity	NPC56329
0.9624	High Similarity	NPC90615
0.9624	High Similarity	NPC25111
0.9621	High Similarity	NPC313081
0.9621	High Similarity	NPC241241
0.9552	High Similarity	NPC243759
0.9552	High Similarity	NPC184613
0.9552	High Similarity	NPC220344
0.9552	High Similarity	NPC243996
0.9552	High Similarity	NPC132804
0.9552	High Similarity	NPC105847
0.9552	High Similarity	NPC275061
0.9552	High Similarity	NPC218131
0.9549	High Similarity	NPC300846
0.9549	High Similarity	NPC114155
0.9549	High Similarity	NPC476639
0.9549	High Similarity	NPC30632
0.9478	High Similarity	NPC151656
0.9478	High Similarity	NPC266006
0.9478	High Similarity	NPC230919
0.9478	High Similarity	NPC22902
0.9478	High Similarity	NPC266453
0.9478	High Similarity	NPC200935
0.9474	High Similarity	NPC283009
0.9474	High Similarity	NPC261873
0.9474	High Similarity	NPC111655
0.9407	High Similarity	NPC114171
0.9407	High Similarity	NPC6300
0.9407	High Similarity	NPC230124
0.9398	High Similarity	NPC103967
0.9398	High Similarity	NPC209199
0.9394	High Similarity	NPC6451
0.9394	High Similarity	NPC161958
0.9394	High Similarity	NPC14224
0.9389	High Similarity	NPC234488
0.9389	High Similarity	NPC126836
0.9389	High Similarity	NPC299221
0.9389	High Similarity	NPC311680
0.9389	High Similarity	NPC51840
0.9343	High Similarity	NPC183709
0.9323	High Similarity	NPC32778
0.9318	High Similarity	NPC232275
0.9318	High Similarity	NPC12275
0.9318	High Similarity	NPC474356
0.9318	High Similarity	NPC45715
0.9313	High Similarity	NPC58164
0.9313	High Similarity	NPC10225
0.9254	High Similarity	NPC289258
0.9254	High Similarity	NPC7515
0.9254	High Similarity	NPC555
0.9254	High Similarity	NPC56764
0.9254	High Similarity	NPC206737
0.9254	High Similarity	NPC188378
0.9254	High Similarity	NPC276026
0.9254	High Similarity	NPC469659
0.9248	High Similarity	NPC218884
0.9242	High Similarity	NPC224157
0.9242	High Similarity	NPC192687
0.9237	High Similarity	NPC266691
0.9237	High Similarity	NPC154866
0.9214	High Similarity	NPC112251
0.9209	High Similarity	NPC50250
0.9185	High Similarity	NPC214853
0.9185	High Similarity	NPC240279
0.9185	High Similarity	NPC180602
0.9185	High Similarity	NPC256262
0.9185	High Similarity	NPC55239
0.9173	High Similarity	NPC15543
0.9167	High Similarity	NPC190144
0.916	High Similarity	NPC124452
0.916	High Similarity	NPC82679
0.916	High Similarity	NPC159968
0.916	High Similarity	NPC236791
0.916	High Similarity	NPC471986
0.916	High Similarity	NPC324112
0.916	High Similarity	NPC169474
0.916	High Similarity	NPC266555
0.916	High Similarity	NPC74817
0.916	High Similarity	NPC293054
0.916	High Similarity	NPC246620
0.916	High Similarity	NPC282000
0.9149	High Similarity	NPC262297
0.9137	High Similarity	NPC469630
0.913	High Similarity	NPC472089
0.9124	High Similarity	NPC127218
0.9124	High Similarity	NPC319647
0.9124	High Similarity	NPC245207
0.9124	High Similarity	NPC25966
0.9118	High Similarity	NPC133025
0.9111	High Similarity	NPC311256
0.9104	High Similarity	NPC228843
0.9091	High Similarity	NPC28765
0.9084	High Similarity	NPC214406
0.9084	High Similarity	NPC44748
0.9084	High Similarity	NPC78974
0.9084	High Similarity	NPC223953
0.9084	High Similarity	NPC223136
0.9084	High Similarity	NPC28730
0.9084	High Similarity	NPC170485
0.9084	High Similarity	NPC103823
0.9084	High Similarity	NPC18924
0.9078	High Similarity	NPC33832
0.9078	High Similarity	NPC126291
0.9065	High Similarity	NPC191231
0.9065	High Similarity	NPC472088
0.9065	High Similarity	NPC472087
0.9065	High Similarity	NPC470917
0.9058	High Similarity	NPC472091
0.9058	High Similarity	NPC472092
0.9058	High Similarity	NPC259519
0.9058	High Similarity	NPC472090
0.9051	High Similarity	NPC86605
0.9051	High Similarity	NPC46277
0.9051	High Similarity	NPC156948
0.9051	High Similarity	NPC107551
0.9051	High Similarity	NPC276490
0.9051	High Similarity	NPC474282
0.9051	High Similarity	NPC326797
0.9051	High Similarity	NPC301765
0.9051	High Similarity	NPC102904
0.9051	High Similarity	NPC3072
0.9051	High Similarity	NPC176051
0.9051	High Similarity	NPC103976
0.903	High Similarity	NPC149337
0.903	High Similarity	NPC471983
0.9015	High Similarity	NPC21563
0.9015	High Similarity	NPC252131
0.9015	High Similarity	NPC127587
0.9015	High Similarity	NPC236760
0.9008	High Similarity	NPC472093
0.9008	High Similarity	NPC208950
0.9008	High Similarity	NPC299584
0.9008	High Similarity	NPC57490
0.9008	High Similarity	NPC265483
0.9008	High Similarity	NPC116907
0.9008	High Similarity	NPC221077
0.9008	High Similarity	NPC475169
0.9008	High Similarity	NPC105925
0.9008	High Similarity	NPC251855
0.9008	High Similarity	NPC60885
0.9008	High Similarity	NPC105718
0.9008	High Similarity	NPC82483
0.9008	High Similarity	NPC117214
0.9008	High Similarity	NPC233410
0.9008	High Similarity	NPC278955
0.9008	High Similarity	NPC234400
0.9008	High Similarity	NPC203133
0.9008	High Similarity	NPC298757
0.9008	High Similarity	NPC193544
0.9008	High Similarity	NPC17943
0.8993	High Similarity	NPC265075
0.8993	High Similarity	NPC471389
0.8986	High Similarity	NPC260741
0.8986	High Similarity	NPC32630
0.8986	High Similarity	NPC70682
0.8986	High Similarity	NPC55947
0.8986	High Similarity	NPC471183
0.8978	High Similarity	NPC472334
0.8978	High Similarity	NPC472336
0.8978	High Similarity	NPC234952
0.8978	High Similarity	NPC162659
0.8978	High Similarity	NPC173660
0.8978	High Similarity	NPC248727
0.8978	High Similarity	NPC265433
0.8978	High Similarity	NPC270456
0.8971	High Similarity	NPC106215
0.8963	High Similarity	NPC127624
0.8963	High Similarity	NPC86655
0.8963	High Similarity	NPC202762
0.8955	High Similarity	NPC214860
0.8947	High Similarity	NPC23012
0.8944	High Similarity	NPC233980
0.8939	High Similarity	NPC112596
0.8939	High Similarity	NPC76451
0.8936	High Similarity	NPC469795

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 NPC212942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	957
0.2-0.3	1789
0.3-0.4	2845
0.4-0.5	1565
0.5-0.6	852
0.6-0.7	609
0.7-0.8	105
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD3027	Phase 3
0.8667	High Similarity	NPD1529	Clinical (unspecified phase)
0.8593	High Similarity	NPD1530	Clinical (unspecified phase)
0.8551	High Similarity	NPD1613	Approved
0.8551	High Similarity	NPD1612	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4625	Phase 3
0.8143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4908	Phase 1
0.8129	Intermediate Similarity	NPD6234	Discontinued
0.8089	Intermediate Similarity	NPD6232	Discontinued
0.8058	Intermediate Similarity	NPD3018	Phase 2
0.8039	Intermediate Similarity	NPD37	Approved
0.8028	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3620	Phase 2
0.7987	Intermediate Similarity	NPD2801	Approved
0.795	Intermediate Similarity	NPD5844	Phase 1
0.7937	Intermediate Similarity	NPD7473	Discontinued
0.7899	Intermediate Similarity	NPD2983	Phase 2
0.7899	Intermediate Similarity	NPD2982	Phase 2
0.7885	Intermediate Similarity	NPD4967	Phase 2
0.7885	Intermediate Similarity	NPD4965	Approved
0.7885	Intermediate Similarity	NPD4966	Approved
0.7883	Intermediate Similarity	NPD1610	Phase 2
0.7879	Intermediate Similarity	NPD5283	Phase 1
0.7863	Intermediate Similarity	NPD228	Approved
0.7826	Intermediate Similarity	NPD2981	Phase 2
0.7806	Intermediate Similarity	NPD1934	Approved
0.7801	Intermediate Similarity	NPD2861	Phase 2
0.7778	Intermediate Similarity	NPD7228	Approved
0.777	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4749	Approved
0.7756	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1548	Phase 1
0.7718	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6674	Discontinued
0.7662	Intermediate Similarity	NPD1653	Approved
0.7655	Intermediate Similarity	NPD4060	Phase 1
0.7647	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7199	Phase 2
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6166	Phase 2
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD3705	Approved
0.75	Intermediate Similarity	NPD4005	Discontinued
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3540	Phase 1
0.7465	Intermediate Similarity	NPD6696	Suspended
0.7438	Intermediate Similarity	NPD3882	Suspended
0.7432	Intermediate Similarity	NPD4097	Suspended
0.7419	Intermediate Similarity	NPD1512	Approved
0.7407	Intermediate Similarity	NPD7635	Approved
0.74	Intermediate Similarity	NPD3539	Phase 1
0.7391	Intermediate Similarity	NPD4055	Discovery
0.7386	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6671	Approved
0.7357	Intermediate Similarity	NPD4626	Approved
0.7353	Intermediate Similarity	NPD8053	Approved
0.7353	Intermediate Similarity	NPD8054	Approved
0.7313	Intermediate Similarity	NPD4750	Phase 3
0.7301	Intermediate Similarity	NPD5494	Approved
0.7297	Intermediate Similarity	NPD1558	Phase 1
0.7292	Intermediate Similarity	NPD3094	Phase 2
0.7285	Intermediate Similarity	NPD6099	Approved
0.7285	Intermediate Similarity	NPD2935	Discontinued
0.7285	Intermediate Similarity	NPD6100	Approved
0.7283	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD3817	Phase 2
0.7262	Intermediate Similarity	NPD7074	Phase 3
0.7256	Intermediate Similarity	NPD6959	Discontinued
0.7254	Intermediate Similarity	NPD1611	Approved
0.7251	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5735	Approved
0.7248	Intermediate Similarity	NPD3657	Discovery
0.7246	Intermediate Similarity	NPD3818	Discontinued
0.7244	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4624	Approved
0.7235	Intermediate Similarity	NPD7549	Discontinued
0.7233	Intermediate Similarity	NPD4380	Phase 2
0.7226	Intermediate Similarity	NPD7124	Phase 2
0.7225	Intermediate Similarity	NPD7906	Approved
0.7222	Intermediate Similarity	NPD8651	Approved
0.7209	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3750	Approved
0.7202	Intermediate Similarity	NPD7054	Approved
0.7197	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4357	Discontinued
0.7179	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD940	Approved
0.7176	Intermediate Similarity	NPD846	Approved
0.7168	Intermediate Similarity	NPD4663	Approved
0.7164	Intermediate Similarity	NPD2342	Discontinued
0.7163	Intermediate Similarity	NPD1651	Approved
0.7162	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5109	Approved
0.7162	Intermediate Similarity	NPD5111	Phase 2
0.7162	Intermediate Similarity	NPD5110	Phase 2
0.716	Intermediate Similarity	NPD7472	Approved
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7143	Intermediate Similarity	NPD5177	Phase 3
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7447	Phase 1
0.7133	Intermediate Similarity	NPD3092	Approved
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7125	Intermediate Similarity	NPD4678	Approved
0.7125	Intermediate Similarity	NPD4675	Approved
0.7124	Intermediate Similarity	NPD7266	Discontinued
0.7124	Intermediate Similarity	NPD5763	Approved
0.7124	Intermediate Similarity	NPD5762	Approved
0.7108	Intermediate Similarity	NPD7229	Phase 3
0.7108	Intermediate Similarity	NPD3787	Discontinued
0.7105	Intermediate Similarity	NPD1510	Phase 2
0.7103	Intermediate Similarity	NPD1283	Approved
0.7101	Intermediate Similarity	NPD1398	Phase 1
0.7099	Intermediate Similarity	NPD1242	Phase 1
0.7099	Intermediate Similarity	NPD7819	Suspended
0.7099	Intermediate Similarity	NPD5929	Approved
0.7097	Intermediate Similarity	NPD3892	Phase 2
0.7097	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7095	Approved
0.7093	Intermediate Similarity	NPD4577	Approved
0.7093	Intermediate Similarity	NPD4578	Approved
0.7086	Intermediate Similarity	NPD1607	Approved
0.7081	Intermediate Similarity	NPD5090	Approved
0.7081	Intermediate Similarity	NPD5089	Approved
0.7078	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7340	Approved
0.707	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7213	Phase 3
0.707	Intermediate Similarity	NPD7212	Phase 2
0.707	Intermediate Similarity	NPD7041	Phase 2
0.7067	Intermediate Similarity	NPD2238	Phase 2
0.7067	Intermediate Similarity	NPD1240	Approved
0.7051	Intermediate Similarity	NPD2677	Approved
0.7051	Intermediate Similarity	NPD6190	Approved
0.7051	Intermediate Similarity	NPD2219	Phase 1
0.7051	Intermediate Similarity	NPD5241	Discontinued
0.7042	Intermediate Similarity	NPD5691	Approved
0.7039	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4536	Approved
0.7039	Intermediate Similarity	NPD4538	Approved
0.7039	Intermediate Similarity	NPD6111	Discontinued
0.7034	Intermediate Similarity	NPD5327	Phase 3
0.7034	Intermediate Similarity	NPD1669	Approved
0.7032	Intermediate Similarity	NPD3060	Approved
0.7025	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2532	Approved
0.7025	Intermediate Similarity	NPD2533	Approved
0.7025	Intermediate Similarity	NPD2534	Approved
0.7024	Intermediate Similarity	NPD27	Approved
0.7024	Intermediate Similarity	NPD2489	Approved
0.7018	Intermediate Similarity	NPD6797	Phase 2
0.7018	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1091	Approved
0.7012	Intermediate Similarity	NPD7768	Phase 2
0.7007	Intermediate Similarity	NPD6584	Phase 3
0.7006	Intermediate Similarity	NPD3051	Approved
0.7	Intermediate Similarity	NPD2674	Phase 3
0.7	Intermediate Similarity	NPD7157	Approved
0.7	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6994	Remote Similarity	NPD7312	Approved
0.6994	Remote Similarity	NPD7313	Approved
0.6994	Remote Similarity	NPD7310	Approved
0.6994	Remote Similarity	NPD7311	Approved
0.6985	Remote Similarity	NPD2684	Approved
0.6977	Remote Similarity	NPD6559	Discontinued
0.6977	Remote Similarity	NPD7251	Discontinued
0.6972	Remote Similarity	NPD3091	Approved
0.697	Remote Similarity	NPD7075	Discontinued
0.6966	Remote Similarity	NPD2232	Approved
0.6966	Remote Similarity	NPD2230	Approved
0.6966	Remote Similarity	NPD2233	Approved
0.6964	Remote Similarity	NPD2970	Approved
0.6964	Remote Similarity	NPD2969	Approved
0.6963	Remote Similarity	NPD968	Approved
0.6962	Remote Similarity	NPD7390	Discontinued
0.6961	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7309	Approved
0.6954	Remote Similarity	NPD4140	Approved
0.6954	Remote Similarity	NPD943	Approved
0.6951	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8252	Approved
0.6941	Remote Similarity	NPD8251	Approved
0.6941	Remote Similarity	NPD3751	Discontinued
0.6941	Remote Similarity	NPD8099	Discontinued

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