NPASS Compound

Structure

CID56329 OpenBabel06191715392D 21 23 0 0 0 0 0 0 0 0999 V2000 1.7321 -0.0000 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 -5.1962 0.0000 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 -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 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 -3.4641 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 -3.4641 0.0000 0.0000 C 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 -2.0000 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 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	296.261
LogP:	3.682
LogD:	3.273
LogS:	-3.828
# 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:	0.89
Synthetic Accessibility Score:	2.611
Fsp3:	0.294
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:	-4.889
MDCK Permeability:	1.84845739568118e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	97.80753326416016%
Volume Distribution (VD):	0.5
Pgp-substrate:	2.1553192138671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.919
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.449
CYP2C19-substrate:	0.343
CYP2C9-inhibitor:	0.28
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.441
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.394
CYP3A4-substrate:	0.48

ADMET: Excretion

Clearance (CL):	7.982
Half-life (T1/2):	0.417

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.242
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.306
Skin Sensitization:	0.74
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.861
Respiratory Toxicity:	0.584

Download Data

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

Natural Product: NPC56329

Natural Product ID:	NPC56329
*Common Name:**	Stemanthrene A
IUPAC Name:	1,5-dimethoxy-6-methyl-9,10-dihydrophenanthrene-2,7-diol
Synonyms:
Standard InCHIKey:	MIBIOCIGEBKGGP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-9-14(19)8-10-4-5-12-11(15(10)16(9)20-2)6-7-13(18)17(12)21-3/h6-8,18-19H,4-5H2,1-3H3
SMILES:	COc1c(O)ccc2c1CCc1c2c(OC)c(c(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480658
PubChem CID:	641760
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
NPO33266	stemona cf. pierrei gagnep.	Species	Stemonaceae	Eukaryota	n.a.	East Thailand, Sri Sa Ket Province, between Sri Sa Ket and Surin	n.a.	PMID[15679323]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12104	Stemona cf. pierrei	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	8500.0	nM	PMID[496528]

☑ 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 NPC56329 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	471
0.1-0.2	1876
0.2-0.3	5132
0.3-0.4	12822
0.4-0.5	4765
0.5-0.6	3874
0.6-0.7	7081
0.7-0.8	5237
0.8-0.85	800
0.85-0.9	409
0.9-0.95	190
0.95-1	40

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC242715
0.9924	High Similarity	NPC275061
0.9924	High Similarity	NPC220344
0.9924	High Similarity	NPC243996
0.9924	High Similarity	NPC132804
0.9923	High Similarity	NPC30632
0.9848	High Similarity	NPC308768
0.9848	High Similarity	NPC12668
0.9847	High Similarity	NPC200935
0.9847	High Similarity	NPC230919
0.9847	High Similarity	NPC266453
0.9847	High Similarity	NPC22902
0.9846	High Similarity	NPC241241
0.9846	High Similarity	NPC108198
0.9846	High Similarity	NPC294884
0.9846	High Similarity	NPC158142
0.9846	High Similarity	NPC200557
0.9846	High Similarity	NPC69029
0.9846	High Similarity	NPC10314
0.9773	High Similarity	NPC218131
0.9773	High Similarity	NPC243759
0.9773	High Similarity	NPC105847
0.9771	High Similarity	NPC202846
0.9771	High Similarity	NPC143139
0.9769	High Similarity	NPC125649
0.9701	High Similarity	NPC183709
0.9701	High Similarity	NPC175838
0.9697	High Similarity	NPC151656
0.9697	High Similarity	NPC266006
0.9695	High Similarity	NPC313081
0.9624	High Similarity	NPC29868
0.9624	High Similarity	NPC212942
0.9624	High Similarity	NPC79622
0.9618	High Similarity	NPC160697
0.9552	High Similarity	NPC34431
0.9552	High Similarity	NPC73505
0.9552	High Similarity	NPC295719
0.9552	High Similarity	NPC165026
0.9478	High Similarity	NPC184613
0.9474	High Similarity	NPC205442
0.947	High Similarity	NPC209199
0.9466	High Similarity	NPC161958
0.9466	High Similarity	NPC228843
0.9466	High Similarity	NPC14224
0.9462	High Similarity	NPC126836
0.9403	High Similarity	NPC272157
0.9403	High Similarity	NPC90615
0.9403	High Similarity	NPC73535
0.9403	High Similarity	NPC25111
0.9403	High Similarity	NPC6262
0.9403	High Similarity	NPC201145
0.9394	High Similarity	NPC32778
0.9389	High Similarity	NPC149337
0.9389	High Similarity	NPC471983
0.9389	High Similarity	NPC15543
0.9338	High Similarity	NPC472089
0.9333	High Similarity	NPC6300
0.9333	High Similarity	NPC230124
0.9333	High Similarity	NPC114171
0.9328	High Similarity	NPC300846
0.9328	High Similarity	NPC114155
0.9328	High Similarity	NPC476639
0.9308	High Similarity	NPC28765
0.9308	High Similarity	NPC154866
0.9281	High Similarity	NPC126291
0.9275	High Similarity	NPC469795
0.927	High Similarity	NPC470917
0.927	High Similarity	NPC472087
0.927	High Similarity	NPC472088
0.9254	High Similarity	NPC261873
0.9254	High Similarity	NPC283009
0.9254	High Similarity	NPC111655
0.9254	High Similarity	NPC256262
0.9231	High Similarity	NPC471986
0.9231	High Similarity	NPC124452
0.9231	High Similarity	NPC293054
0.9231	High Similarity	NPC282000
0.9231	High Similarity	NPC74817
0.9231	High Similarity	NPC159968
0.9231	High Similarity	NPC246620
0.9231	High Similarity	NPC236791
0.9231	High Similarity	NPC324112
0.9231	High Similarity	NPC169474
0.9231	High Similarity	NPC266555
0.9231	High Similarity	NPC252131
0.9231	High Similarity	NPC236760
0.9231	High Similarity	NPC82679
0.9214	High Similarity	NPC262297
0.9197	High Similarity	NPC265075
0.9179	High Similarity	NPC188378
0.9179	High Similarity	NPC206737
0.9179	High Similarity	NPC555
0.9179	High Similarity	NPC469659
0.9179	High Similarity	NPC56764
0.9179	High Similarity	NPC289258
0.9179	High Similarity	NPC103967
0.9179	High Similarity	NPC276026
0.9179	High Similarity	NPC7515
0.916	High Similarity	NPC23012
0.916	High Similarity	NPC215300
0.9154	High Similarity	NPC223136
0.9154	High Similarity	NPC28730
0.9154	High Similarity	NPC103823
0.9154	High Similarity	NPC214406
0.9154	High Similarity	NPC223953
0.9154	High Similarity	NPC44748
0.9154	High Similarity	NPC18924
0.9154	High Similarity	NPC170485
0.9154	High Similarity	NPC78974
0.9143	High Similarity	NPC233980
0.913	High Similarity	NPC191231
0.9124	High Similarity	NPC472092
0.9124	High Similarity	NPC472090
0.9124	High Similarity	NPC472091
0.9118	High Similarity	NPC35550
0.9111	High Similarity	NPC55239
0.9111	High Similarity	NPC214853
0.9111	High Similarity	NPC240279
0.9111	High Similarity	NPC180602
0.9098	High Similarity	NPC282508
0.9084	High Similarity	NPC21563
0.9084	High Similarity	NPC127587
0.9084	High Similarity	NPC53781
0.9078	High Similarity	NPC474397
0.9077	High Similarity	NPC298757
0.9077	High Similarity	NPC251855
0.9077	High Similarity	NPC117214
0.9077	High Similarity	NPC60885
0.9077	High Similarity	NPC203133
0.9077	High Similarity	NPC233410
0.9077	High Similarity	NPC82483
0.9077	High Similarity	NPC472093
0.9077	High Similarity	NPC193544
0.9077	High Similarity	NPC17943
0.9077	High Similarity	NPC105031
0.9077	High Similarity	NPC299584
0.9077	High Similarity	NPC208950
0.9077	High Similarity	NPC475169
0.9077	High Similarity	NPC221077
0.9077	High Similarity	NPC234400
0.9077	High Similarity	NPC265483
0.9077	High Similarity	NPC105925
0.9077	High Similarity	NPC116907
0.9077	High Similarity	NPC57490
0.9065	High Similarity	NPC469630
0.9058	High Similarity	NPC71046
0.9051	High Similarity	NPC260741
0.9051	High Similarity	NPC32630
0.9051	High Similarity	NPC55947
0.9051	High Similarity	NPC70682
0.9044	High Similarity	NPC133025
0.9037	High Similarity	NPC311256
0.903	High Similarity	NPC218884
0.903	High Similarity	NPC6451
0.9023	High Similarity	NPC311680
0.9023	High Similarity	NPC51840
0.9023	High Similarity	NPC299221
0.9023	High Similarity	NPC234488
0.9015	High Similarity	NPC38017
0.9008	High Similarity	NPC76451
0.9	High Similarity	NPC473845
0.9	High Similarity	NPC50250
0.9	High Similarity	NPC473108
0.9	High Similarity	NPC228503
0.9	High Similarity	NPC5796
0.9	High Similarity	NPC138248
0.9	High Similarity	NPC206487
0.9	High Similarity	NPC224342
0.8986	High Similarity	NPC266650
0.8986	High Similarity	NPC198038
0.8986	High Similarity	NPC234568
0.8978	High Similarity	NPC46277
0.8978	High Similarity	NPC3072
0.8978	High Similarity	NPC156948
0.8978	High Similarity	NPC301765
0.8978	High Similarity	NPC86605
0.8971	High Similarity	NPC37410
0.8963	High Similarity	NPC36661
0.8955	High Similarity	NPC45715
0.8955	High Similarity	NPC232275
0.8955	High Similarity	NPC474356
0.8955	High Similarity	NPC12275
0.8947	High Similarity	NPC212015
0.8947	High Similarity	NPC58164
0.8947	High Similarity	NPC10225
0.8939	High Similarity	NPC473221
0.8931	High Similarity	NPC113495
0.8931	High Similarity	NPC266705
0.8931	High Similarity	NPC228771
0.8931	High Similarity	NPC105718
0.8931	High Similarity	NPC278955
0.8931	High Similarity	NPC29008
0.8923	High Similarity	NPC282496
0.8923	High Similarity	NPC233526
0.8923	High Similarity	NPC197757
0.8923	High Similarity	NPC95168
0.8923	High Similarity	NPC136319
0.8923	High Similarity	NPC84086
0.8923	High Similarity	NPC228922
0.8923	High Similarity	NPC121115

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 NPC56329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	994
0.2-0.3	1731
0.3-0.4	2805
0.4-0.5	1593
0.5-0.6	854
0.6-0.7	632
0.7-0.8	114
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8806	High Similarity	NPD3027	Phase 3
0.8667	High Similarity	NPD4625	Phase 3
0.8593	High Similarity	NPD1529	Clinical (unspecified phase)
0.8519	High Similarity	NPD1530	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6232	Discontinued
0.8188	Intermediate Similarity	NPD4908	Phase 1
0.8116	Intermediate Similarity	NPD3018	Phase 2
0.8101	Intermediate Similarity	NPD7473	Discontinued
0.8085	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD3620	Phase 2
0.8065	Intermediate Similarity	NPD6234	Discontinued
0.7974	Intermediate Similarity	NPD37	Approved
0.7956	Intermediate Similarity	NPD4749	Approved
0.7956	Intermediate Similarity	NPD2982	Phase 2
0.7956	Intermediate Similarity	NPD2983	Phase 2
0.7956	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1610	Phase 2
0.7939	Intermediate Similarity	NPD5283	Phase 1
0.7923	Intermediate Similarity	NPD228	Approved
0.7914	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6674	Discontinued
0.7891	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5844	Phase 1
0.7883	Intermediate Similarity	NPD2981	Phase 2
0.7832	Intermediate Similarity	NPD4060	Phase 1
0.7821	Intermediate Similarity	NPD4966	Approved
0.7821	Intermediate Similarity	NPD4967	Phase 2
0.7821	Intermediate Similarity	NPD4965	Approved
0.7817	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1548	Phase 1
0.7742	Intermediate Similarity	NPD1934	Approved
0.7724	Intermediate Similarity	NPD4097	Suspended
0.7716	Intermediate Similarity	NPD7228	Approved
0.7698	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2801	Approved
0.7664	Intermediate Similarity	NPD4626	Approved
0.7634	Intermediate Similarity	NPD3021	Approved
0.7634	Intermediate Similarity	NPD3022	Approved
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7548	Intermediate Similarity	NPD4005	Discontinued
0.7531	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3540	Phase 1
0.75	Intermediate Similarity	NPD4750	Phase 3
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3882	Suspended
0.7483	Intermediate Similarity	NPD2861	Phase 2
0.7481	Intermediate Similarity	NPD2342	Discontinued
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7468	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1651	Approved
0.7451	Intermediate Similarity	NPD1511	Approved
0.745	Intermediate Similarity	NPD3539	Phase 1
0.745	Intermediate Similarity	NPD6100	Approved
0.745	Intermediate Similarity	NPD6099	Approved
0.7438	Intermediate Similarity	NPD4055	Discovery
0.7429	Intermediate Similarity	NPD3705	Approved
0.7407	Intermediate Similarity	NPD6959	Discontinued
0.74	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8053	Approved
0.7396	Intermediate Similarity	NPD8054	Approved
0.7394	Intermediate Similarity	NPD1283	Approved
0.7394	Intermediate Similarity	NPD8651	Approved
0.7394	Intermediate Similarity	NPD6696	Suspended
0.7372	Intermediate Similarity	NPD1653	Approved
0.7355	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1512	Approved
0.7347	Intermediate Similarity	NPD1558	Phase 1
0.7338	Intermediate Similarity	NPD5691	Approved
0.7333	Intermediate Similarity	NPD7635	Approved
0.732	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3657	Discovery
0.7297	Intermediate Similarity	NPD5735	Approved
0.7294	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4624	Approved
0.729	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4380	Phase 2
0.7273	Intermediate Similarity	NPD7124	Phase 2
0.7255	Intermediate Similarity	NPD3750	Approved
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7819	Suspended
0.7248	Intermediate Similarity	NPD1607	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.7231	Intermediate Similarity	NPD940	Approved
0.7226	Intermediate Similarity	NPD7041	Phase 2
0.7226	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4357	Discontinued
0.7225	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3094	Phase 2
0.7219	Intermediate Similarity	NPD7240	Approved
0.7211	Intermediate Similarity	NPD5109	Approved
0.7211	Intermediate Similarity	NPD5110	Phase 2
0.7211	Intermediate Similarity	NPD5111	Phase 2
0.7211	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3817	Phase 2
0.7203	Intermediate Similarity	NPD1669	Approved
0.7202	Intermediate Similarity	NPD7074	Phase 3
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5536	Phase 2
0.7186	Intermediate Similarity	NPD3818	Discontinued
0.7183	Intermediate Similarity	NPD1281	Approved
0.7183	Intermediate Similarity	NPD1611	Approved
0.7183	Intermediate Similarity	NPD422	Phase 1
0.7183	Intermediate Similarity	NPD3092	Approved
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD7447	Phase 1
0.7179	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2532	Approved
0.7171	Intermediate Similarity	NPD5762	Approved
0.7171	Intermediate Similarity	NPD5763	Approved
0.716	Intermediate Similarity	NPD7768	Phase 2
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7134	Intermediate Similarity	NPD5494	Approved
0.7125	Intermediate Similarity	NPD5090	Approved
0.7125	Intermediate Similarity	NPD5089	Approved
0.7124	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7117	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7075	Discontinued
0.7115	Intermediate Similarity	NPD7213	Phase 3
0.7115	Intermediate Similarity	NPD7390	Discontinued
0.7115	Intermediate Similarity	NPD7212	Phase 2
0.7114	Intermediate Similarity	NPD1240	Approved
0.7105	Intermediate Similarity	NPD2438	Suspended
0.7105	Intermediate Similarity	NPD2935	Discontinued
0.7101	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5241	Discontinued
0.7086	Intermediate Similarity	NPD4536	Approved
0.7086	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4538	Approved
0.7086	Intermediate Similarity	NPD6111	Discontinued
0.7083	Intermediate Similarity	NPD5327	Phase 3
0.7078	Intermediate Similarity	NPD5177	Phase 3
0.7078	Intermediate Similarity	NPD3060	Approved
0.707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7906	Approved
0.7067	Intermediate Similarity	NPD5124	Phase 1
0.7067	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD27	Approved
0.7066	Intermediate Similarity	NPD2489	Approved
0.7063	Intermediate Similarity	NPD4675	Approved
0.7063	Intermediate Similarity	NPD4678	Approved
0.7059	Intermediate Similarity	NPD7266	Discontinued
0.7055	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6584	Phase 3
0.7052	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7157	Approved
0.705	Intermediate Similarity	NPD709	Approved
0.705	Intermediate Similarity	NPD6671	Approved
0.7048	Intermediate Similarity	NPD3051	Approved
0.7047	Intermediate Similarity	NPD2674	Phase 3
0.7042	Intermediate Similarity	NPD2286	Discontinued
0.7042	Intermediate Similarity	NPD5125	Phase 3
0.7042	Intermediate Similarity	NPD5126	Approved
0.7039	Intermediate Similarity	NPD4108	Discontinued
0.7037	Intermediate Similarity	NPD2684	Approved
0.7037	Intermediate Similarity	NPD5929	Approved
0.7037	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4578	Approved
0.7035	Intermediate Similarity	NPD4577	Approved
0.7032	Intermediate Similarity	NPD6331	Phase 2
0.703	Intermediate Similarity	NPD4666	Phase 3
0.7029	Intermediate Similarity	NPD1398	Phase 1
0.7029	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3091	Approved
0.7011	Intermediate Similarity	NPD4663	Approved
0.7006	Intermediate Similarity	NPD2969	Approved
0.7006	Intermediate Similarity	NPD2970	Approved
0.7	Intermediate Similarity	NPD2238	Phase 2
0.7	Intermediate Similarity	NPD7340	Approved
0.7	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD943	Approved
0.7	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6987	Remote Similarity	NPD2219	Phase 1
0.6987	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2677	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