NPASS Compound

Structure

CID121910 OpenBabel06191715472D 25 28 0 0 1 0 0 0 0 0999 V2000 6.0622 -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 0.0000 -3.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 5.1962 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 3.4641 0.0000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 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 3 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 20 1 0 0 0 0 11 25 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 17 2 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.07
Volume:	326.098
LogP:	2.21
LogD:	1.902
LogS:	-3.72
# Rotatable Bonds:	1
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	3.606
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007
MDCK Permeability:	5.471792519529117e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.395
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.235

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	96.44329071044922%
Volume Distribution (VD):	0.555
Pgp-substrate:	4.624507904052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.671
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.65
CYP2C9-substrate:	0.72
CYP2D6-inhibitor:	0.321
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	1.605
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.742
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.743
Skin Sensitization:	0.622
Carcinogencity:	0.643
Eye Corrosion:	0.006
Eye Irritation:	0.888
Respiratory Toxicity:	0.353

Download Data

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

Natural Product: NPC121910

Natural Product ID:	NPC121910
*Common Name:**	Boeravinone D
IUPAC Name:	3,9,11-trihydroxy-6-methoxy-10-methyl-6H-chromeno[3,4-b]chromen-12-one
Synonyms:	Boeravinone D
Standard InCHIKey:	ZESAOJOQKPXOPG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O7/c1-7-10(20)6-12-14(15(7)21)16(22)13-9-4-3-8(19)5-11(9)25-18(23-2)17(13)24-12/h3-6,18-21H,1-2H3
SMILES:	COC1Oc2cc(O)ccc2c2c1oc1cc(O)c(c(c1c2=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498456
PubChem CID:	15081178
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	roots	n.a.	n.a.	PMID[16792408]
NPO33416	boerhaavia diffusa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23914900]
NPO18025	Boerhavia diffusa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18025	Boerhavia diffusa	Species	Nyctaginaceae	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
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	4770.0	nM	PMID[493694]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	5010.0	nM	PMID[493694]

☑ 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 NPC121910 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	436
0.1-0.2	1846
0.2-0.3	4192
0.3-0.4	10058
0.4-0.5	8265
0.5-0.6	4046
0.6-0.7	5775
0.7-0.8	4079
0.8-0.85	2713
0.85-0.9	1217
0.9-0.95	63
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168805
0.9863	High Similarity	NPC471291
0.9797	High Similarity	NPC92395
0.9797	High Similarity	NPC87404
0.9595	High Similarity	NPC470771
0.9595	High Similarity	NPC471289
0.9419	High Similarity	NPC470773
0.9355	High Similarity	NPC470772
0.9351	High Similarity	NPC470756
0.929	High Similarity	NPC44947
0.929	High Similarity	NPC131745
0.9262	High Similarity	NPC266572
0.9241	High Similarity	NPC471287
0.9231	High Similarity	NPC124155
0.9231	High Similarity	NPC66087
0.9231	High Similarity	NPC278419
0.9231	High Similarity	NPC179198
0.9231	High Similarity	NPC183672
0.9231	High Similarity	NPC257566
0.9226	High Similarity	NPC471290
0.9226	High Similarity	NPC47923
0.9221	High Similarity	NPC73511
0.9205	High Similarity	NPC318424
0.9195	High Similarity	NPC97716
0.9195	High Similarity	NPC237635
0.9195	High Similarity	NPC201731
0.9195	High Similarity	NPC104406
0.9195	High Similarity	NPC79469
0.9195	High Similarity	NPC24673
0.9189	High Similarity	NPC319752
0.9177	High Similarity	NPC471288
0.9167	High Similarity	NPC259834
0.9161	High Similarity	NPC472320
0.9156	High Similarity	NPC313163
0.9156	High Similarity	NPC23817
0.9156	High Similarity	NPC161749
0.9156	High Similarity	NPC258035
0.9156	High Similarity	NPC197896
0.9156	High Similarity	NPC156457
0.915	High Similarity	NPC27408
0.915	High Similarity	NPC470605
0.915	High Similarity	NPC470604
0.915	High Similarity	NPC470603
0.915	High Similarity	NPC95090
0.9139	High Similarity	NPC471984
0.9133	High Similarity	NPC6511
0.9128	High Similarity	NPC474161
0.9128	High Similarity	NPC476088
0.911	High Similarity	NPC78913
0.911	High Similarity	NPC18260
0.9103	High Similarity	NPC303913
0.9091	High Similarity	NPC211482
0.9091	High Similarity	NPC45165
0.9091	High Similarity	NPC476652
0.9091	High Similarity	NPC206378
0.9085	High Similarity	NPC210003
0.9085	High Similarity	NPC83283
0.9085	High Similarity	NPC39360
0.9085	High Similarity	NPC143851
0.9085	High Similarity	NPC211158
0.9085	High Similarity	NPC268950
0.9085	High Similarity	NPC29763
0.9085	High Similarity	NPC108706
0.9085	High Similarity	NPC78021
0.9085	High Similarity	NPC87304
0.9085	High Similarity	NPC106625
0.9079	High Similarity	NPC325429
0.9073	High Similarity	NPC5173
0.9067	High Similarity	NPC473077
0.9067	High Similarity	NPC296998
0.906	High Similarity	NPC311741
0.906	High Similarity	NPC234629
0.9054	High Similarity	NPC293852
0.9054	High Similarity	NPC59739
0.9054	High Similarity	NPC299080
0.9054	High Similarity	NPC266725
0.9054	High Similarity	NPC78803
0.9054	High Similarity	NPC217083
0.9054	High Similarity	NPC62840
0.9054	High Similarity	NPC214236
0.9048	High Similarity	NPC159275
0.9048	High Similarity	NPC241100
0.9048	High Similarity	NPC101366
0.9045	High Similarity	NPC93215
0.9045	High Similarity	NPC190450
0.9041	High Similarity	NPC201395
0.9032	High Similarity	NPC60966
0.9032	High Similarity	NPC473512
0.9032	High Similarity	NPC6985
0.9032	High Similarity	NPC182634
0.9032	High Similarity	NPC470606
0.9032	High Similarity	NPC108831
0.9032	High Similarity	NPC65003
0.9032	High Similarity	NPC129827
0.9032	High Similarity	NPC44931
0.9026	High Similarity	NPC476169
0.9026	High Similarity	NPC26195
0.9026	High Similarity	NPC72649
0.9026	High Similarity	NPC470681
0.9026	High Similarity	NPC169248
0.9026	High Similarity	NPC97052
0.9026	High Similarity	NPC99233
0.9026	High Similarity	NPC39351
0.902	High Similarity	NPC161881
0.902	High Similarity	NPC121001
0.902	High Similarity	NPC150123
0.902	High Similarity	NPC166067
0.902	High Similarity	NPC56232
0.902	High Similarity	NPC10807
0.902	High Similarity	NPC244583
0.902	High Similarity	NPC259182
0.9013	High Similarity	NPC188403
0.9013	High Similarity	NPC29777
0.9013	High Similarity	NPC471115
0.9007	High Similarity	NPC244407
0.9007	High Similarity	NPC321623
0.9007	High Similarity	NPC189087
0.9007	High Similarity	NPC161191
0.9	High Similarity	NPC111786
0.9	High Similarity	NPC83357
0.9	High Similarity	NPC67805
0.9	High Similarity	NPC267375
0.9	High Similarity	NPC301276
0.9	High Similarity	NPC195621
0.9	High Similarity	NPC5319
0.9	High Similarity	NPC142405
0.9	High Similarity	NPC475052
0.9	High Similarity	NPC88964
0.9	High Similarity	NPC214774
0.9	High Similarity	NPC20488
0.9	High Similarity	NPC176229
0.9	High Similarity	NPC246948
0.9	High Similarity	NPC470647
0.9	High Similarity	NPC312973
0.9	High Similarity	NPC54577
0.8993	High Similarity	NPC242100
0.8993	High Similarity	NPC255133
0.8993	High Similarity	NPC219915
0.8986	High Similarity	NPC3188
0.8986	High Similarity	NPC52789
0.8986	High Similarity	NPC4743
0.8986	High Similarity	NPC268204
0.8986	High Similarity	NPC312391
0.8986	High Similarity	NPC324386
0.8986	High Similarity	NPC213322
0.8986	High Similarity	NPC282300
0.8986	High Similarity	NPC110969
0.8986	High Similarity	NPC55832
0.8986	High Similarity	NPC26051
0.8981	High Similarity	NPC94155
0.898	High Similarity	NPC96565
0.898	High Similarity	NPC301217
0.898	High Similarity	NPC217186
0.898	High Similarity	NPC303633
0.898	High Similarity	NPC295384
0.898	High Similarity	NPC53181
0.898	High Similarity	NPC55018
0.898	High Similarity	NPC216978
0.898	High Similarity	NPC220062
0.8974	High Similarity	NPC473634
0.8974	High Similarity	NPC320283
0.8974	High Similarity	NPC472459
0.8974	High Similarity	NPC308265
0.8974	High Similarity	NPC138811
0.8974	High Similarity	NPC111929
0.8974	High Similarity	NPC104677
0.8974	High Similarity	NPC43761
0.8974	High Similarity	NPC470607
0.8974	High Similarity	NPC22062
0.8974	High Similarity	NPC41121
0.8968	High Similarity	NPC261866
0.8968	High Similarity	NPC307938
0.8968	High Similarity	NPC127406
0.8968	High Similarity	NPC203500
0.8968	High Similarity	NPC170475
0.8968	High Similarity	NPC323593
0.8961	High Similarity	NPC472583
0.8961	High Similarity	NPC223701
0.8961	High Similarity	NPC311579
0.8961	High Similarity	NPC7989
0.8961	High Similarity	NPC469405
0.8961	High Similarity	NPC236756
0.8954	High Similarity	NPC471675
0.8954	High Similarity	NPC328740
0.8954	High Similarity	NPC209846
0.8954	High Similarity	NPC477897
0.8954	High Similarity	NPC289774
0.8947	High Similarity	NPC317492
0.8944	High Similarity	NPC150767
0.8944	High Similarity	NPC78734
0.8944	High Similarity	NPC76047
0.894	High Similarity	NPC166757
0.894	High Similarity	NPC110303
0.894	High Similarity	NPC308200
0.894	High Similarity	NPC23728
0.894	High Similarity	NPC14001
0.894	High Similarity	NPC283234
0.8933	High Similarity	NPC224714
0.8933	High Similarity	NPC273538
0.8933	High Similarity	NPC216538

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 NPC121910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	942
0.2-0.3	1796
0.3-0.4	2687
0.4-0.5	1878
0.5-0.6	959
0.6-0.7	303
0.7-0.8	128
0.8-0.85	46
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9156	High Similarity	NPD4381	Clinical (unspecified phase)
0.9	High Similarity	NPD7804	Clinical (unspecified phase)
0.8933	High Similarity	NPD4378	Clinical (unspecified phase)
0.8766	High Similarity	NPD4380	Phase 2
0.8716	High Similarity	NPD1552	Clinical (unspecified phase)
0.8716	High Similarity	NPD1550	Clinical (unspecified phase)
0.8707	High Similarity	NPD1510	Phase 2
0.8704	High Similarity	NPD3818	Discontinued
0.8684	High Similarity	NPD7410	Clinical (unspecified phase)
0.8671	High Similarity	NPD7075	Discontinued
0.8658	High Similarity	NPD1549	Phase 2
0.865	High Similarity	NPD7054	Approved
0.8599	High Similarity	NPD2393	Clinical (unspecified phase)
0.8599	High Similarity	NPD7096	Clinical (unspecified phase)
0.8598	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD7074	Phase 3
0.859	High Similarity	NPD7411	Suspended
0.8545	High Similarity	NPD6797	Phase 2
0.8544	High Similarity	NPD8443	Clinical (unspecified phase)
0.8535	High Similarity	NPD6801	Discontinued
0.8535	High Similarity	NPD1934	Approved
0.8523	High Similarity	NPD2796	Approved
0.8494	Intermediate Similarity	NPD7251	Discontinued
0.8481	Intermediate Similarity	NPD2801	Approved
0.8443	Intermediate Similarity	NPD7808	Phase 3
0.8443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1240	Approved
0.8383	Intermediate Similarity	NPD6559	Discontinued
0.8377	Intermediate Similarity	NPD1511	Approved
0.8377	Intermediate Similarity	NPD6799	Approved
0.8365	Intermediate Similarity	NPD7819	Suspended
0.8322	Intermediate Similarity	NPD1607	Approved
0.8301	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD3750	Approved
0.8269	Intermediate Similarity	NPD1512	Approved
0.8261	Intermediate Similarity	NPD7768	Phase 2
0.8261	Intermediate Similarity	NPD3882	Suspended
0.8242	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5403	Approved
0.8205	Intermediate Similarity	NPD5401	Approved
0.8199	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8117	Intermediate Similarity	NPD2800	Approved
0.8117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD5494	Approved
0.8101	Intermediate Similarity	NPD920	Approved
0.8098	Intermediate Similarity	NPD3749	Approved
0.8086	Intermediate Similarity	NPD5402	Approved
0.8061	Intermediate Similarity	NPD6959	Discontinued
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1551	Phase 2
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD1243	Approved
0.7976	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD3748	Approved
0.7962	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2313	Discontinued
0.7895	Intermediate Similarity	NPD5953	Discontinued
0.7888	Intermediate Similarity	NPD7458	Discontinued
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7853	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD919	Approved
0.7806	Intermediate Similarity	NPD2935	Discontinued
0.7803	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7584	Approved
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD8313	Approved
0.7759	Intermediate Similarity	NPD8312	Approved
0.7756	Intermediate Similarity	NPD2344	Approved
0.7738	Intermediate Similarity	NPD1247	Approved
0.7727	Intermediate Similarity	NPD6651	Approved
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3226	Approved
0.7667	Intermediate Similarity	NPD2798	Approved
0.7662	Intermediate Similarity	NPD1933	Approved
0.7628	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3751	Discontinued
0.76	Intermediate Similarity	NPD1203	Approved
0.7597	Intermediate Similarity	NPD943	Approved
0.759	Intermediate Similarity	NPD1465	Phase 2
0.759	Intermediate Similarity	NPD8455	Phase 2
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4908	Phase 1
0.7562	Intermediate Similarity	NPD2309	Approved
0.7554	Intermediate Similarity	NPD6776	Approved
0.7554	Intermediate Similarity	NPD6780	Approved
0.7554	Intermediate Similarity	NPD6777	Approved
0.7554	Intermediate Similarity	NPD6778	Approved
0.7554	Intermediate Similarity	NPD6779	Approved
0.7554	Intermediate Similarity	NPD6781	Approved
0.7554	Intermediate Similarity	NPD6782	Approved
0.7548	Intermediate Similarity	NPD5124	Phase 1
0.7548	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1548	Phase 1
0.7533	Intermediate Similarity	NPD3225	Approved
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7473	Intermediate Similarity	NPD4363	Phase 3
0.7473	Intermediate Similarity	NPD4360	Phase 2
0.7468	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.745	Intermediate Similarity	NPD422	Phase 1
0.745	Intermediate Similarity	NPD1610	Phase 2
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3926	Phase 2
0.7433	Intermediate Similarity	NPD7435	Discontinued
0.7433	Intermediate Similarity	NPD7698	Approved
0.7433	Intermediate Similarity	NPD7696	Phase 3
0.7433	Intermediate Similarity	NPD7697	Approved
0.7425	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7405	Intermediate Similarity	NPD4308	Phase 3
0.74	Intermediate Similarity	NPD9717	Approved
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7394	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD7871	Phase 2
0.7368	Intermediate Similarity	NPD2797	Approved
0.7368	Intermediate Similarity	NPD7585	Approved
0.7365	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7390	Discontinued
0.7358	Intermediate Similarity	NPD6099	Approved
0.7358	Intermediate Similarity	NPD6100	Approved
0.7344	Intermediate Similarity	NPD7783	Phase 2
0.7344	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4288	Approved
0.7337	Intermediate Similarity	NPD4361	Phase 2
0.7325	Intermediate Similarity	NPD447	Suspended
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7316	Intermediate Similarity	NPD7583	Approved
0.7314	Intermediate Similarity	NPD7228	Approved
0.7299	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1653	Approved
0.7287	Intermediate Similarity	NPD6823	Phase 2
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD6534	Approved
0.7283	Intermediate Similarity	NPD5711	Approved
0.7283	Intermediate Similarity	NPD6535	Approved
0.7277	Intermediate Similarity	NPD7701	Phase 2
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3267	Approved
0.7255	Intermediate Similarity	NPD3266	Approved
0.7247	Intermediate Similarity	NPD7685	Pre-registration
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7874	Approved
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7182	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD9545	Approved
0.7171	Intermediate Similarity	NPD1608	Approved
0.7166	Intermediate Similarity	NPD7699	Phase 2
0.7166	Intermediate Similarity	NPD7700	Phase 2
0.7165	Intermediate Similarity	NPD7801	Approved
0.7161	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5889	Approved
0.716	Intermediate Similarity	NPD5890	Approved
0.7158	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1729	Discontinued
0.7134	Intermediate Similarity	NPD1296	Phase 2
0.7134	Intermediate Similarity	NPD3764	Approved
0.7117	Intermediate Similarity	NPD2654	Approved
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7105	Intermediate Similarity	NPD1091	Approved
0.7073	Intermediate Similarity	NPD7003	Approved
0.707	Intermediate Similarity	NPD4625	Phase 3
0.7055	Intermediate Similarity	NPD2424	Discontinued
0.7049	Intermediate Similarity	NPD8434	Phase 2
0.7047	Intermediate Similarity	NPD9493	Approved
0.7044	Intermediate Similarity	NPD4060	Phase 1
0.7043	Intermediate Similarity	NPD6213	Phase 3

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