NPASS Compound

Structure

NPC12668 OpenBabel07101719512D 22 24 0 0 0 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 -2.5000 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 0.8660 -2.5000 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 -1.7321 0.0000 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 -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 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 -0.0000 -4.0000 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 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 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:	300.1
Volume:	302.415
LogP:	3.568
LogD:	3.253
LogS:	-4.123
# Rotatable Bonds:	3
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	2.471
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.932
MDCK Permeability:	2.6327070372644812e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	90.5568618774414%
Volume Distribution (VD):	0.546
Pgp-substrate:	12.021106719970703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.408
CYP2C19-substrate:	0.502
CYP2C9-inhibitor:	0.518
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.607
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.36
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	10.508
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.796
AMES Toxicity:	0.656
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.665
Skin Sensitization:	0.943
Carcinogencity:	0.17
Eye Corrosion:	0.183
Eye Irritation:	0.975
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC12668

Natural Product ID:	NPC12668
*Common Name:**	Fimbriol A
IUPAC Name:	3,4,9-trimethoxyphenanthrene-2,5-diol
Synonyms:	Fimbriol A
Standard InCHIKey:	MRYYPHKLLLULDL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-20-13-8-9-7-12(19)16(21-2)17(22-3)14(9)15-10(13)5-4-6-11(15)18/h4-8,18-19H,1-3H3
SMILES:	COc1cc2cc(c(c(c2c2c1cccc2O)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208382
PubChem CID:	11335575
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
NPO19381	Maxillaria densa	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479332]
NPO19381	Maxillaria densa	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234371]
NPO19381	Maxillaria densa	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
EC50	2
Others	2

Activity Type	# Activity
Tissue	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	EC50	=	288500.0	nM	PMID[526017]
NPT177	Tissue	Aorta	Rattus norvegicus	EC50	=	234000.0	nM	PMID[526017]
NPT177	Tissue	Aorta	Rattus norvegicus	Efficacy	=	83.05	%	PMID[526017]
NPT177	Tissue	Aorta	Rattus norvegicus	Efficacy	=	73.86	%	PMID[526017]

☑ 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 NPC12668 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	563
0.1-0.2	1987
0.2-0.3	5636
0.3-0.4	12676
0.4-0.5	4507
0.5-0.6	3981
0.6-0.7	7123
0.7-0.8	5047
0.8-0.85	669
0.85-0.9	376
0.9-0.95	98
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC308768
0.9924	High Similarity	NPC275061
0.9924	High Similarity	NPC220344
0.9924	High Similarity	NPC243996
0.9924	High Similarity	NPC218131
0.9924	High Similarity	NPC243759
0.9924	High Similarity	NPC105847
0.9924	High Similarity	NPC132804
0.9851	High Similarity	NPC175838
0.9848	High Similarity	NPC151656
0.9848	High Similarity	NPC56329
0.9848	High Similarity	NPC200935
0.9848	High Similarity	NPC230919
0.9848	High Similarity	NPC266453
0.9848	High Similarity	NPC266006
0.9848	High Similarity	NPC242715
0.9848	High Similarity	NPC22902
0.9773	High Similarity	NPC202846
0.9773	High Similarity	NPC30632
0.9773	High Similarity	NPC143139
0.9704	High Similarity	NPC183709
0.9701	High Similarity	NPC295719
0.9701	High Similarity	NPC73505
0.9701	High Similarity	NPC165026
0.9701	High Similarity	NPC34431
0.9697	High Similarity	NPC69029
0.9697	High Similarity	NPC200557
0.9697	High Similarity	NPC294884
0.9697	High Similarity	NPC241241
0.9697	High Similarity	NPC158142
0.9697	High Similarity	NPC108198
0.9697	High Similarity	NPC10314
0.9627	High Similarity	NPC29868
0.9627	High Similarity	NPC212942
0.9627	High Similarity	NPC79622
0.9621	High Similarity	NPC160697
0.9621	High Similarity	NPC125649
0.9552	High Similarity	NPC73535
0.9552	High Similarity	NPC25111
0.9552	High Similarity	NPC90615
0.9552	High Similarity	NPC201145
0.9552	High Similarity	NPC6262
0.9552	High Similarity	NPC272157
0.9549	High Similarity	NPC313081
0.9481	High Similarity	NPC184613
0.9478	High Similarity	NPC300846
0.9478	High Similarity	NPC476639
0.9478	High Similarity	NPC114155
0.9478	High Similarity	NPC205442
0.947	High Similarity	NPC228843
0.9424	High Similarity	NPC126291
0.9403	High Similarity	NPC111655
0.9403	High Similarity	NPC283009
0.9403	High Similarity	NPC261873
0.9394	High Similarity	NPC149337
0.9394	High Similarity	NPC471983
0.9357	High Similarity	NPC262297
0.9343	High Similarity	NPC472089
0.9338	High Similarity	NPC114171
0.9338	High Similarity	NPC6300
0.9338	High Similarity	NPC230124
0.9328	High Similarity	NPC209199
0.9328	High Similarity	NPC103967
0.9323	High Similarity	NPC161958
0.9323	High Similarity	NPC14224
0.9318	High Similarity	NPC126836
0.9275	High Similarity	NPC472088
0.9275	High Similarity	NPC472087
0.9275	High Similarity	NPC470917
0.9259	High Similarity	NPC256262
0.9254	High Similarity	NPC32778
0.9248	High Similarity	NPC15543
0.9209	High Similarity	NPC469630
0.9203	High Similarity	NPC265075
0.9185	High Similarity	NPC289258
0.9185	High Similarity	NPC7515
0.9185	High Similarity	NPC276026
0.9185	High Similarity	NPC188378
0.9185	High Similarity	NPC555
0.9185	High Similarity	NPC206737
0.9185	High Similarity	NPC56764
0.9185	High Similarity	NPC469659
0.9179	High Similarity	NPC218884
0.9167	High Similarity	NPC28765
0.9167	High Similarity	NPC154866
0.9167	High Similarity	NPC38017
0.9167	High Similarity	NPC215300
0.9167	High Similarity	NPC23012
0.9149	High Similarity	NPC233980
0.9143	High Similarity	NPC469795
0.913	High Similarity	NPC472092
0.913	High Similarity	NPC472091
0.913	High Similarity	NPC472090
0.9118	High Similarity	NPC55239
0.9118	High Similarity	NPC180602
0.9118	High Similarity	NPC214853
0.9118	High Similarity	NPC240279
0.9104	High Similarity	NPC282508
0.9091	High Similarity	NPC236791
0.9091	High Similarity	NPC124452
0.9091	High Similarity	NPC471986
0.9091	High Similarity	NPC21563
0.9091	High Similarity	NPC252131
0.9091	High Similarity	NPC236760
0.9091	High Similarity	NPC159968
0.9091	High Similarity	NPC74817
0.9091	High Similarity	NPC324112
0.9091	High Similarity	NPC53781
0.9091	High Similarity	NPC266555
0.9091	High Similarity	NPC82679
0.9091	High Similarity	NPC293054
0.9091	High Similarity	NPC246620
0.9091	High Similarity	NPC282000
0.9091	High Similarity	NPC169474
0.9085	High Similarity	NPC474397
0.9058	High Similarity	NPC32630
0.9058	High Similarity	NPC55947
0.9058	High Similarity	NPC70682
0.9058	High Similarity	NPC260741
0.9051	High Similarity	NPC472647
0.9051	High Similarity	NPC191462
0.9051	High Similarity	NPC170328
0.9051	High Similarity	NPC472649
0.9051	High Similarity	NPC133463
0.9051	High Similarity	NPC133025
0.9051	High Similarity	NPC472648
0.9051	High Similarity	NPC206525
0.9044	High Similarity	NPC311256
0.9037	High Similarity	NPC303144
0.9037	High Similarity	NPC6451
0.903	High Similarity	NPC51840
0.903	High Similarity	NPC311680
0.903	High Similarity	NPC234488
0.903	High Similarity	NPC299221
0.9015	High Similarity	NPC223136
0.9015	High Similarity	NPC170485
0.9015	High Similarity	NPC78974
0.9015	High Similarity	NPC223953
0.9015	High Similarity	NPC28730
0.9015	High Similarity	NPC18924
0.9015	High Similarity	NPC103823
0.9015	High Similarity	NPC214406
0.9015	High Similarity	NPC44748
0.9007	High Similarity	NPC473845
0.9007	High Similarity	NPC50250
0.9007	High Similarity	NPC473108
0.9	High Similarity	NPC191231
0.8993	High Similarity	NPC266650
0.8986	High Similarity	NPC156948
0.8986	High Similarity	NPC86605
0.8986	High Similarity	NPC35550
0.8986	High Similarity	NPC71465
0.8986	High Similarity	NPC472646
0.8986	High Similarity	NPC46277
0.8986	High Similarity	NPC3072
0.8986	High Similarity	NPC301765
0.8978	High Similarity	NPC37410
0.8978	High Similarity	NPC258780
0.8963	High Similarity	NPC45715
0.8963	High Similarity	NPC232275
0.8963	High Similarity	NPC474356
0.8963	High Similarity	NPC12275
0.8955	High Similarity	NPC58164
0.8955	High Similarity	NPC10225
0.8947	High Similarity	NPC473221
0.8947	High Similarity	NPC127587
0.8939	High Similarity	NPC221077
0.8939	High Similarity	NPC113495
0.8939	High Similarity	NPC17943
0.8939	High Similarity	NPC208950
0.8939	High Similarity	NPC105031
0.8939	High Similarity	NPC299584
0.8939	High Similarity	NPC475169
0.8939	High Similarity	NPC82483
0.8939	High Similarity	NPC116907
0.8939	High Similarity	NPC234400
0.8939	High Similarity	NPC60885
0.8939	High Similarity	NPC193544
0.8939	High Similarity	NPC203133
0.8939	High Similarity	NPC233410
0.8939	High Similarity	NPC298757
0.8939	High Similarity	NPC57490
0.8939	High Similarity	NPC117214
0.8939	High Similarity	NPC105718
0.8939	High Similarity	NPC278955
0.8939	High Similarity	NPC105925
0.8939	High Similarity	NPC251855
0.8939	High Similarity	NPC265483
0.8939	High Similarity	NPC472093
0.8929	High Similarity	NPC35216
0.8929	High Similarity	NPC19158
0.8929	High Similarity	NPC71046
0.8921	High Similarity	NPC22517
0.8921	High Similarity	NPC471183
0.8913	High Similarity	NPC234952
0.8913	High Similarity	NPC162659
0.8913	High Similarity	NPC270456
0.8913	High Similarity	NPC265433
0.8913	High Similarity	NPC248727
0.8897	High Similarity	NPC86655

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 NPC12668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	483
0.1-0.2	977
0.2-0.3	1790
0.3-0.4	2791
0.4-0.5	1593
0.5-0.6	868
0.6-0.7	546
0.7-0.8	94
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8815	High Similarity	NPD3027	Phase 3
0.8603	High Similarity	NPD1529	Clinical (unspecified phase)
0.854	High Similarity	NPD4625	Phase 3
0.8529	High Similarity	NPD1530	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD1613	Approved
0.8489	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6232	Discontinued
0.8345	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7473	Discontinued
0.8201	Intermediate Similarity	NPD4908	Phase 1
0.8077	Intermediate Similarity	NPD6234	Discontinued
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD3018	Phase 2
0.7987	Intermediate Similarity	NPD37	Approved
0.7972	Intermediate Similarity	NPD3620	Phase 2
0.7972	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6674	Discontinued
0.7905	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD2983	Phase 2
0.7842	Intermediate Similarity	NPD2982	Phase 2
0.7842	Intermediate Similarity	NPD4749	Approved
0.7842	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD4965	Approved
0.7834	Intermediate Similarity	NPD4967	Phase 2
0.7834	Intermediate Similarity	NPD4966	Approved
0.7826	Intermediate Similarity	NPD1610	Phase 2
0.7821	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD5283	Phase 1
0.7803	Intermediate Similarity	NPD228	Approved
0.7801	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2981	Phase 2
0.7756	Intermediate Similarity	NPD1934	Approved
0.773	Intermediate Similarity	NPD7228	Approved
0.7724	Intermediate Similarity	NPD4060	Phase 1
0.7708	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2801	Approved
0.7664	Intermediate Similarity	NPD1548	Phase 1
0.764	Intermediate Similarity	NPD7199	Phase 2
0.7619	Intermediate Similarity	NPD4097	Suspended
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6166	Phase 2
0.7589	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4626	Approved
0.7546	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6959	Discontinued
0.7519	Intermediate Similarity	NPD3022	Approved
0.7519	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD2342	Discontinued
0.75	Intermediate Similarity	NPD2861	Phase 2
0.7484	Intermediate Similarity	NPD1465	Phase 2
0.7468	Intermediate Similarity	NPD1511	Approved
0.7452	Intermediate Similarity	NPD4005	Discontinued
0.7447	Intermediate Similarity	NPD3705	Approved
0.7417	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3540	Phase 1
0.7413	Intermediate Similarity	NPD6696	Suspended
0.7412	Intermediate Similarity	NPD8053	Approved
0.7412	Intermediate Similarity	NPD8054	Approved
0.7391	Intermediate Similarity	NPD3882	Suspended
0.7389	Intermediate Similarity	NPD1653	Approved
0.7388	Intermediate Similarity	NPD4750	Phase 3
0.7372	Intermediate Similarity	NPD1512	Approved
0.7372	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1651	Approved
0.7353	Intermediate Similarity	NPD7635	Approved
0.7351	Intermediate Similarity	NPD6099	Approved
0.7351	Intermediate Similarity	NPD6100	Approved
0.7351	Intermediate Similarity	NPD3539	Phase 1
0.7346	Intermediate Similarity	NPD4055	Discovery
0.7341	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4380	Phase 2
0.7292	Intermediate Similarity	NPD1283	Approved
0.7292	Intermediate Similarity	NPD8651	Approved
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7248	Intermediate Similarity	NPD1558	Phase 1
0.7244	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7041	Phase 2
0.7244	Intermediate Similarity	NPD7390	Discontinued
0.7244	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3094	Phase 2
0.7235	Intermediate Similarity	NPD6559	Discontinued
0.7235	Intermediate Similarity	NPD7240	Approved
0.7234	Intermediate Similarity	NPD5691	Approved
0.7222	Intermediate Similarity	NPD3817	Phase 2
0.7219	Intermediate Similarity	NPD7074	Phase 3
0.7215	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1611	Approved
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.72	Intermediate Similarity	NPD3657	Discovery
0.72	Intermediate Similarity	NPD5735	Approved
0.7197	Intermediate Similarity	NPD2533	Approved
0.7197	Intermediate Similarity	NPD2532	Approved
0.7197	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7447	Phase 1
0.7197	Intermediate Similarity	NPD2534	Approved
0.7192	Intermediate Similarity	NPD4624	Approved
0.7179	Intermediate Similarity	NPD7124	Phase 2
0.7178	Intermediate Similarity	NPD7768	Phase 2
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3750	Approved
0.7161	Intermediate Similarity	NPD7003	Approved
0.716	Intermediate Similarity	NPD7819	Suspended
0.716	Intermediate Similarity	NPD7054	Approved
0.7152	Intermediate Similarity	NPD1607	Approved
0.7152	Intermediate Similarity	NPD5494	Approved
0.7134	Intermediate Similarity	NPD4357	Discontinued
0.7134	Intermediate Similarity	NPD7213	Phase 3
0.7134	Intermediate Similarity	NPD7212	Phase 2
0.7134	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2935	Discontinued
0.7121	Intermediate Similarity	NPD940	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7118	Intermediate Similarity	NPD7472	Approved
0.7117	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5109	Approved
0.7114	Intermediate Similarity	NPD5111	Phase 2
0.7114	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5110	Phase 2
0.7105	Intermediate Similarity	NPD4536	Approved
0.7105	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4538	Approved
0.7103	Intermediate Similarity	NPD1669	Approved
0.7097	Intermediate Similarity	NPD5177	Phase 3
0.7093	Intermediate Similarity	NPD7549	Discontinued
0.7093	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5536	Phase 2
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7906	Approved
0.7083	Intermediate Similarity	NPD3092	Approved
0.7083	Intermediate Similarity	NPD1281	Approved
0.7083	Intermediate Similarity	NPD422	Phase 1
0.7081	Intermediate Similarity	NPD4678	Approved
0.7081	Intermediate Similarity	NPD4675	Approved
0.7078	Intermediate Similarity	NPD7266	Discontinued
0.7078	Intermediate Similarity	NPD5762	Approved
0.7078	Intermediate Similarity	NPD5763	Approved
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6584	Phase 3
0.7073	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6671	Approved
0.7069	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5126	Approved
0.7063	Intermediate Similarity	NPD2286	Discontinued
0.7063	Intermediate Similarity	NPD5125	Phase 3
0.7059	Intermediate Similarity	NPD1510	Phase 2
0.7059	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5929	Approved
0.7052	Intermediate Similarity	NPD4577	Approved
0.7052	Intermediate Similarity	NPD4578	Approved
0.7051	Intermediate Similarity	NPD3892	Phase 2
0.705	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1398	Phase 1
0.7048	Intermediate Similarity	NPD6746	Phase 2
0.7047	Intermediate Similarity	NPD7095	Approved
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7037	Intermediate Similarity	NPD5089	Approved
0.7037	Intermediate Similarity	NPD5090	Approved
0.7032	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7075	Discontinued
0.7029	Intermediate Similarity	NPD4663	Approved
0.7021	Intermediate Similarity	NPD7340	Approved
0.702	Intermediate Similarity	NPD2979	Phase 3
0.702	Intermediate Similarity	NPD1240	Approved
0.702	Intermediate Similarity	NPD2238	Phase 2
0.7019	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2438	Suspended
0.7013	Intermediate Similarity	NPD5405	Approved
0.7013	Intermediate Similarity	NPD5404	Approved
0.7013	Intermediate Similarity	NPD5406	Approved
0.7013	Intermediate Similarity	NPD5408	Approved
0.7007	Intermediate Similarity	NPD5451	Approved
0.7006	Intermediate Similarity	NPD5241	Discontinued
0.7006	Intermediate Similarity	NPD2677	Approved
0.7006	Intermediate Similarity	NPD2219	Phase 1
0.7	Intermediate Similarity	NPD8099	Discontinued
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD8252	Approved
0.7	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8251	Approved
0.6993	Remote Similarity	NPD6111	Discontinued
0.6987	Remote Similarity	NPD3060	Approved
0.6986	Remote Similarity	NPD5327	Phase 3
0.6982	Remote Similarity	NPD27	Approved
0.6982	Remote Similarity	NPD2489	Approved
0.6977	Remote Similarity	NPD6797	Phase 2
0.6974	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5124	Phase 1
0.697	Remote Similarity	NPD6788	Approved
0.6966	Remote Similarity	NPD1091	Approved
0.6964	Remote Similarity	NPD3787	Discontinued
0.6964	Remote Similarity	NPD3051	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