NPASS Compound

Structure

CID275061 OpenBabel06191716082D 22 24 0 0 0 0 0 0 0 0999 V2000 5.1962 1.0000 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 -0.8660 1.5000 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 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 2.5981 1.5000 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 -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 2.5981 -0.5000 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 3.4641 1.0000 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 3.4641 0.0000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 0.0000 1.0000 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 22 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 13 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 11 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.29
Volume:	550.221
LogP:	0.562
LogD:	-0.137
LogS:	-3.116
# Rotatable Bonds:	4
TPSA:	193.44
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.236
Synthetic Accessibility Score:	5.649
Fsp3:	0.862
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.681
MDCK Permeability:	4.925940447719768e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.907
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	53.586524963378906%
Volume Distribution (VD):	0.395
Pgp-substrate:	25.870149612426758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.771
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.164
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.201
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	1.975
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.51
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.814
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.357
Carcinogencity:	0.877
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC275061

Natural Product ID:	NPC275061
*Common Name:**	2,5,6-Trimethoxyphenanthrene-1,7-Diol
IUPAC Name:	2,5,6-trimethoxyphenanthrene-1,7-diol
Synonyms:
Standard InCHIKey:	QRWFGIYPPNJHCO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-20-13-7-6-10-11(15(13)19)5-4-9-8-12(18)16(21-2)17(22-3)14(9)10/h4-8,18-19H,1-3H3
SMILES:	COc1ccc2c(ccc3cc(c(c(c23)OC)OC)O)c1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254598
PubChem CID:	24762423
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO3894	Dendrobium nobile	Species	Orchidaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	54100.0	nM	PMID[522707]

☑ 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 NPC275061 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	564
0.1-0.2	2017
0.2-0.3	5763
0.3-0.4	12799
0.4-0.5	4275
0.5-0.6	3954
0.6-0.7	7250
0.7-0.8	4958
0.8-0.85	646
0.85-0.9	339
0.9-0.95	98
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC243996
1.0	High Similarity	NPC132804
1.0	High Similarity	NPC220344
0.9924	High Similarity	NPC230919
0.9924	High Similarity	NPC266453
0.9924	High Similarity	NPC22902
0.9924	High Similarity	NPC12668
0.9924	High Similarity	NPC242715
0.9924	High Similarity	NPC56329
0.9924	High Similarity	NPC308768
0.9924	High Similarity	NPC200935
0.9848	High Similarity	NPC218131
0.9848	High Similarity	NPC243759
0.9848	High Similarity	NPC105847
0.9847	High Similarity	NPC30632
0.9776	High Similarity	NPC183709
0.9776	High Similarity	NPC175838
0.9773	High Similarity	NPC151656
0.9773	High Similarity	NPC266006
0.9771	High Similarity	NPC69029
0.9771	High Similarity	NPC241241
0.9771	High Similarity	NPC158142
0.9771	High Similarity	NPC10314
0.9771	High Similarity	NPC108198
0.9771	High Similarity	NPC200557
0.9771	High Similarity	NPC294884
0.9697	High Similarity	NPC202846
0.9697	High Similarity	NPC143139
0.9695	High Similarity	NPC125649
0.9627	High Similarity	NPC165026
0.9627	High Similarity	NPC295719
0.9627	High Similarity	NPC73505
0.9627	High Similarity	NPC34431
0.9621	High Similarity	NPC313081
0.9552	High Similarity	NPC79622
0.9552	High Similarity	NPC29868
0.9552	High Similarity	NPC212942
0.9545	High Similarity	NPC160697
0.9542	High Similarity	NPC228843
0.9478	High Similarity	NPC25111
0.9478	High Similarity	NPC6262
0.9478	High Similarity	NPC201145
0.9478	High Similarity	NPC272157
0.9478	High Similarity	NPC90615
0.9478	High Similarity	NPC73535
0.9466	High Similarity	NPC149337
0.9466	High Similarity	NPC471983
0.9412	High Similarity	NPC472089
0.9407	High Similarity	NPC184613
0.9403	High Similarity	NPC476639
0.9403	High Similarity	NPC300846
0.9403	High Similarity	NPC114155
0.9403	High Similarity	NPC205442
0.9398	High Similarity	NPC209199
0.9394	High Similarity	NPC161958
0.9394	High Similarity	NPC14224
0.9389	High Similarity	NPC126836
0.9353	High Similarity	NPC126291
0.9343	High Similarity	NPC472087
0.9343	High Similarity	NPC472088
0.9328	High Similarity	NPC261873
0.9328	High Similarity	NPC283009
0.9328	High Similarity	NPC111655
0.9323	High Similarity	NPC32778
0.9318	High Similarity	NPC15543
0.9286	High Similarity	NPC262297
0.9265	High Similarity	NPC6300
0.9265	High Similarity	NPC114171
0.9265	High Similarity	NPC230124
0.9254	High Similarity	NPC103967
0.9237	High Similarity	NPC28765
0.9237	High Similarity	NPC154866
0.9237	High Similarity	NPC215300
0.9209	High Similarity	NPC469795
0.9203	High Similarity	NPC470917
0.9197	High Similarity	NPC472090
0.9197	High Similarity	NPC472092
0.9197	High Similarity	NPC472091
0.9185	High Similarity	NPC256262
0.9173	High Similarity	NPC282508
0.916	High Similarity	NPC124452
0.916	High Similarity	NPC82679
0.916	High Similarity	NPC236760
0.916	High Similarity	NPC252131
0.916	High Similarity	NPC74817
0.916	High Similarity	NPC159968
0.916	High Similarity	NPC53781
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	NPC293054
0.916	High Similarity	NPC246620
0.916	High Similarity	NPC282000
0.9137	High Similarity	NPC469630
0.913	High Similarity	NPC265075
0.9124	High Similarity	NPC55947
0.9111	High Similarity	NPC206737
0.9111	High Similarity	NPC56764
0.9111	High Similarity	NPC469659
0.9111	High Similarity	NPC188378
0.9111	High Similarity	NPC555
0.9111	High Similarity	NPC276026
0.9111	High Similarity	NPC289258
0.9111	High Similarity	NPC7515
0.9104	High Similarity	NPC218884
0.9091	High Similarity	NPC23012
0.9091	High Similarity	NPC38017
0.9084	High Similarity	NPC18924
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
0.9078	High Similarity	NPC233980
0.9065	High Similarity	NPC191231
0.9051	High Similarity	NPC35550
0.9044	High Similarity	NPC180602
0.9044	High Similarity	NPC214853
0.9044	High Similarity	NPC240279
0.9044	High Similarity	NPC37410
0.9044	High Similarity	NPC55239
0.9015	High Similarity	NPC21563
0.9015	High Similarity	NPC127587
0.9014	High Similarity	NPC474397
0.9008	High Similarity	NPC113495
0.9008	High Similarity	NPC472093
0.9008	High Similarity	NPC208950
0.9008	High Similarity	NPC299584
0.9008	High Similarity	NPC57490
0.9008	High Similarity	NPC105031
0.9008	High Similarity	NPC221077
0.9008	High Similarity	NPC475169
0.9008	High Similarity	NPC265483
0.9008	High Similarity	NPC116907
0.9008	High Similarity	NPC105925
0.9008	High Similarity	NPC298757
0.9008	High Similarity	NPC251855
0.9008	High Similarity	NPC60885
0.9008	High Similarity	NPC117214
0.9008	High Similarity	NPC234400
0.9008	High Similarity	NPC82483
0.9008	High Similarity	NPC233410
0.9008	High Similarity	NPC203133
0.9008	High Similarity	NPC193544
0.9008	High Similarity	NPC17943
0.8993	High Similarity	NPC71046
0.8986	High Similarity	NPC260741
0.8986	High Similarity	NPC32630
0.8986	High Similarity	NPC70682
0.8978	High Similarity	NPC206525
0.8978	High Similarity	NPC472648
0.8978	High Similarity	NPC472649
0.8978	High Similarity	NPC133463
0.8978	High Similarity	NPC133025
0.8978	High Similarity	NPC472647
0.8978	High Similarity	NPC170328
0.8978	High Similarity	NPC191462
0.8971	High Similarity	NPC311256
0.8963	High Similarity	NPC303144
0.8963	High Similarity	NPC6451
0.8955	High Similarity	NPC299221
0.8955	High Similarity	NPC234488
0.8955	High Similarity	NPC311680
0.8955	High Similarity	NPC51840
0.8955	High Similarity	NPC254000
0.8939	High Similarity	NPC76451
0.8936	High Similarity	NPC473845
0.8936	High Similarity	NPC50250
0.8936	High Similarity	NPC473108
0.8931	High Similarity	NPC224342
0.8931	High Similarity	NPC5796
0.8931	High Similarity	NPC138248
0.8931	High Similarity	NPC228503
0.8931	High Similarity	NPC206487
0.8929	High Similarity	NPC277784
0.8921	High Similarity	NPC198038
0.8921	High Similarity	NPC266650
0.8921	High Similarity	NPC234568
0.8913	High Similarity	NPC3072
0.8913	High Similarity	NPC46277
0.8913	High Similarity	NPC301765
0.8913	High Similarity	NPC156948
0.8913	High Similarity	NPC71465
0.8913	High Similarity	NPC472646
0.8913	High Similarity	NPC86605
0.8905	High Similarity	NPC258780
0.8897	High Similarity	NPC36661
0.8889	High Similarity	NPC232275
0.8889	High Similarity	NPC12275
0.8889	High Similarity	NPC45715
0.8889	High Similarity	NPC474356
0.8881	High Similarity	NPC58164
0.8881	High Similarity	NPC212015
0.8881	High Similarity	NPC10225
0.8872	High Similarity	NPC473221

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 NPC275061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	487
0.1-0.2	979
0.2-0.3	1755
0.3-0.4	2802
0.4-0.5	1591
0.5-0.6	883
0.6-0.7	544
0.7-0.8	100
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
0.8741	High Similarity	NPD3027	Phase 3
0.8603	High Similarity	NPD4625	Phase 3
0.8529	High Similarity	NPD1529	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD1613	Approved
0.8417	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8261	Intermediate Similarity	NPD4908	Phase 1
0.8165	Intermediate Similarity	NPD7473	Discontinued
0.8058	Intermediate Similarity	NPD3018	Phase 2
0.8028	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3620	Phase 2
0.8013	Intermediate Similarity	NPD6234	Discontinued
0.795	Intermediate Similarity	NPD5844	Phase 1
0.7922	Intermediate Similarity	NPD37	Approved
0.7899	Intermediate Similarity	NPD2983	Phase 2
0.7899	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD4749	Approved
0.7899	Intermediate Similarity	NPD2982	Phase 2
0.7883	Intermediate Similarity	NPD1610	Phase 2
0.7879	Intermediate Similarity	NPD5283	Phase 1
0.7863	Intermediate Similarity	NPD228	Approved
0.7857	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6674	Discontinued
0.7838	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2981	Phase 2
0.7778	Intermediate Similarity	NPD4060	Phase 1
0.7771	Intermediate Similarity	NPD4967	Phase 2
0.7771	Intermediate Similarity	NPD4966	Approved
0.7771	Intermediate Similarity	NPD4965	Approved
0.7762	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1548	Phase 1
0.7692	Intermediate Similarity	NPD1934	Approved
0.7688	Intermediate Similarity	NPD7199	Phase 2
0.7671	Intermediate Similarity	NPD4097	Suspended
0.7669	Intermediate Similarity	NPD7228	Approved
0.7643	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2801	Approved
0.7609	Intermediate Similarity	NPD4626	Approved
0.7593	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.7557	Intermediate Similarity	NPD2342	Discontinued
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
0.75	Intermediate Similarity	NPD4005	Discontinued
0.7469	Intermediate Similarity	NPD6959	Discontinued
0.7467	Intermediate Similarity	NPD3540	Phase 1
0.7456	Intermediate Similarity	NPD8053	Approved
0.7456	Intermediate Similarity	NPD8054	Approved
0.7444	Intermediate Similarity	NPD4750	Phase 3
0.7438	Intermediate Similarity	NPD3882	Suspended
0.7431	Intermediate Similarity	NPD2861	Phase 2
0.7421	Intermediate Similarity	NPD1465	Phase 2
0.7419	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1651	Approved
0.7403	Intermediate Similarity	NPD1511	Approved
0.74	Intermediate Similarity	NPD6100	Approved
0.74	Intermediate Similarity	NPD3539	Phase 1
0.74	Intermediate Similarity	NPD6099	Approved
0.7391	Intermediate Similarity	NPD4055	Discovery
0.7376	Intermediate Similarity	NPD3705	Approved
0.7351	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6696	Suspended
0.7343	Intermediate Similarity	NPD1283	Approved
0.7343	Intermediate Similarity	NPD8651	Approved
0.7325	Intermediate Similarity	NPD1653	Approved
0.7308	Intermediate Similarity	NPD1512	Approved
0.7308	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1558	Phase 1
0.729	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7041	Phase 2
0.7286	Intermediate Similarity	NPD5691	Approved
0.7283	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7635	Approved
0.7273	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3657	Discovery
0.7248	Intermediate Similarity	NPD5735	Approved
0.7244	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7447	Phase 1
0.7244	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4624	Approved
0.7233	Intermediate Similarity	NPD4380	Phase 2
0.7226	Intermediate Similarity	NPD7124	Phase 2
0.7222	Intermediate Similarity	NPD7768	Phase 2
0.7212	Intermediate Similarity	NPD7229	Phase 3
0.7208	Intermediate Similarity	NPD7003	Approved
0.7208	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3750	Approved
0.7205	Intermediate Similarity	NPD7819	Suspended
0.72	Intermediate Similarity	NPD1607	Approved
0.7179	Intermediate Similarity	NPD4357	Discontinued
0.7179	Intermediate Similarity	NPD7213	Phase 3
0.7179	Intermediate Similarity	NPD7212	Phase 2
0.7179	Intermediate Similarity	NPD7390	Discontinued
0.7176	Intermediate Similarity	NPD7240	Approved
0.7176	Intermediate Similarity	NPD940	Approved
0.7176	Intermediate Similarity	NPD6559	Discontinued
0.7176	Intermediate Similarity	NPD846	Approved
0.7172	Intermediate Similarity	NPD3094	Phase 2
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	NPD7074	Phase 3
0.716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3817	Phase 2
0.7153	Intermediate Similarity	NPD1669	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD2533	Approved
0.7134	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2534	Approved
0.7134	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2532	Approved
0.7133	Intermediate Similarity	NPD3092	Approved
0.7133	Intermediate Similarity	NPD1281	Approved
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7133	Intermediate Similarity	NPD1611	Approved
0.7124	Intermediate Similarity	NPD5763	Approved
0.7124	Intermediate Similarity	NPD5762	Approved
0.7123	Intermediate Similarity	NPD6584	Phase 3
0.7117	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2286	Discontinued
0.7105	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1510	Phase 2
0.7101	Intermediate Similarity	NPD7054	Approved
0.7101	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1242	Phase 1
0.7097	Intermediate Similarity	NPD3892	Phase 2
0.7095	Intermediate Similarity	NPD7095	Approved
0.7091	Intermediate Similarity	NPD5494	Approved
0.7081	Intermediate Similarity	NPD5090	Approved
0.7081	Intermediate Similarity	NPD5089	Approved
0.7078	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7075	Discontinued
0.7067	Intermediate Similarity	NPD1240	Approved
0.7063	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD2438	Suspended
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7059	Intermediate Similarity	NPD7472	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5451	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7051	Intermediate Similarity	NPD5241	Discontinued
0.7047	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6798	Discontinued
0.7041	Intermediate Similarity	NPD8252	Approved
0.7041	Intermediate Similarity	NPD8251	Approved
0.7041	Intermediate Similarity	NPD8099	Discontinued
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
0.7035	Intermediate Similarity	NPD7549	Discontinued
0.7035	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5327	Phase 3
0.7032	Intermediate Similarity	NPD3060	Approved
0.7032	Intermediate Similarity	NPD5177	Phase 3
0.7029	Intermediate Similarity	NPD7906	Approved
0.7024	Intermediate Similarity	NPD27	Approved
0.7024	Intermediate Similarity	NPD2489	Approved
0.702	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5124	Phase 1
0.7019	Intermediate Similarity	NPD4678	Approved
0.7019	Intermediate Similarity	NPD4675	Approved
0.7018	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7266	Discontinued
0.7012	Intermediate Similarity	NPD6788	Approved
0.7011	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3051	Approved
0.7	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD2674	Phase 3
0.7	Intermediate Similarity	NPD7157	Approved
0.7	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD8156	Discontinued
0.6994	Remote Similarity	NPD5929	Approved
0.6994	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4577	Approved
0.6994	Remote Similarity	NPD4578	Approved
0.6993	Remote Similarity	NPD4108	Discontinued
0.6993	Remote Similarity	NPD5126	Approved
0.6993	Remote Similarity	NPD6516	Phase 2
0.6993	Remote Similarity	NPD5125	Phase 3
0.6993	Remote Similarity	NPD5846	Approved
0.6988	Remote Similarity	NPD4666	Phase 3
0.6988	Remote Similarity	NPD6746	Phase 2
0.6987	Remote Similarity	NPD6331	Phase 2

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