NPASS Compound

Structure

NPC146636 OpenBabel07101718292D 33 37 0 0 1 0 0 0 0 0999 V2000 8.9526 1.3672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0614 -0.2922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1066 1.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0032 -1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9691 -1.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7796 0.9495 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 7.7455 1.2083 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 -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 6.5208 -0.0164 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 5.2961 -1.2412 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 7.2279 -0.7235 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5549 -0.2753 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4526 0.5012 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 4.3301 -1.5000 0.0000 C 0 0 1 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1996 -2.4914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8478 0.4319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1938 -0.4647 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 30 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 26 1 0 0 0 0 13 31 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 21 2 0 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 28 2 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.2
Volume:	458.546
LogP:	5.777
LogD:	4.006
LogS:	-3.405
# Rotatable Bonds:	2
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	3.988
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.876
MDCK Permeability:	2.1748915969510563e-05
Pgp-inhibitor:	0.428
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	99.59951782226562%
Volume Distribution (VD):	0.502
Pgp-substrate:	1.0154896974563599%

ADMET: Metabolism

CYP1A2-inhibitor:	0.445
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.612
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.654
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.465
CYP2D6-substrate:	0.576
CYP3A4-inhibitor:	0.724
CYP3A4-substrate:	0.713

ADMET: Excretion

Clearance (CL):	3.839
Half-life (T1/2):	0.035

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.138
Carcinogencity:	0.855
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.082

Download Data

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

Natural Product: NPC146636

Natural Product ID:	NPC146636
*Common Name:**	Sophonorol C
IUPAC Name:	(3S)-3,5-dihydroxy-3-(5-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-8,8-dimethyl-9,10-dihydro-2H-pyrano[2,3-h]chromen-4-one
Synonyms:	Sophonorol C
Standard InCHIKey:	VTNVBSWKRFKHFA-AREMUKBSSA-N
Standard InCHI:	InChI=1S/C26H30O7/c1-24(2)10-8-14-18(32-24)7-6-16(21(14)30-5)26(29)13-31-22-15-9-11-25(3,4)33-19(15)12-17(27)20(22)23(26)28/h6-7,12,27,29H,8-11,13H2,1-5H3/t26-/m1/s1
SMILES:	COc1c2CCC(Oc2ccc1[C@]1(O)COc2c(C1=O)c(O)cc1c2CCC(O1)(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557703
PubChem CID:	44233680
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003527] 8-prenylated isoflavanones

*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
NPO3544	Sophora mollis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19572738]
NPO3544	Sophora mollis	Species	Fabaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	12900.0	nM	PMID[494379]

☑ 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 NPC146636 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	399
0.1-0.2	1554
0.2-0.3	3735
0.3-0.4	9546
0.4-0.5	8937
0.5-0.6	3702
0.6-0.7	5351
0.7-0.8	5111
0.8-0.85	2651
0.85-0.9	1424
0.9-0.95	274
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC476169
0.9664	High Similarity	NPC210597
0.96	High Similarity	NPC209760
0.96	High Similarity	NPC100134
0.9536	High Similarity	NPC471116
0.947	High Similarity	NPC203080
0.9467	High Similarity	NPC471229
0.9463	High Similarity	NPC277032
0.9408	High Similarity	NPC207809
0.9408	High Similarity	NPC259710
0.9408	High Similarity	NPC48579
0.9408	High Similarity	NPC304207
0.9408	High Similarity	NPC217706
0.9404	High Similarity	NPC475790
0.94	High Similarity	NPC267117
0.9342	High Similarity	NPC248793
0.9342	High Similarity	NPC180301
0.9342	High Similarity	NPC236756
0.9342	High Similarity	NPC311579
0.9338	High Similarity	NPC319910
0.9338	High Similarity	NPC254412
0.9338	High Similarity	NPC474021
0.9338	High Similarity	NPC262038
0.9338	High Similarity	NPC474023
0.9338	High Similarity	NPC278476
0.9338	High Similarity	NPC262039
0.9329	High Similarity	NPC472918
0.9299	High Similarity	NPC62261
0.9281	High Similarity	NPC477958
0.9281	High Similarity	NPC111341
0.9281	High Similarity	NPC304745
0.9276	High Similarity	NPC217149
0.9276	High Similarity	NPC171651
0.9276	High Similarity	NPC216035
0.9276	High Similarity	NPC35567
0.9276	High Similarity	NPC243171
0.9276	High Similarity	NPC138288
0.9272	High Similarity	NPC105136
0.9272	High Similarity	NPC471115
0.9272	High Similarity	NPC29777
0.9267	High Similarity	NPC296869
0.9245	High Similarity	NPC326877
0.9245	High Similarity	NPC177480
0.9236	High Similarity	NPC63438
0.9221	High Similarity	NPC215917
0.9221	High Similarity	NPC10754
0.9221	High Similarity	NPC20530
0.9216	High Similarity	NPC472583
0.9216	High Similarity	NPC469405
0.9216	High Similarity	NPC20907
0.9216	High Similarity	NPC268193
0.9216	High Similarity	NPC223701
0.9216	High Similarity	NPC112701
0.9216	High Similarity	NPC244250
0.9216	High Similarity	NPC109594
0.9216	High Similarity	NPC326592
0.9216	High Similarity	NPC7989
0.9216	High Similarity	NPC88983
0.9216	High Similarity	NPC293286
0.9211	High Similarity	NPC263384
0.9211	High Similarity	NPC244577
0.9211	High Similarity	NPC471677
0.9211	High Similarity	NPC471676
0.9211	High Similarity	NPC472636
0.9211	High Similarity	NPC472422
0.9211	High Similarity	NPC472420
0.9205	High Similarity	NPC473016
0.92	High Similarity	NPC308200
0.9187	High Similarity	NPC74559
0.9182	High Similarity	NPC8965
0.9167	High Similarity	NPC471976
0.9156	High Similarity	NPC477530
0.915	High Similarity	NPC150123
0.915	High Similarity	NPC56232
0.915	High Similarity	NPC244583
0.915	High Similarity	NPC473996
0.915	High Similarity	NPC161881
0.915	High Similarity	NPC10807
0.9139	High Similarity	NPC39195
0.9139	High Similarity	NPC145467
0.9139	High Similarity	NPC244407
0.9133	High Similarity	NPC124729
0.9133	High Similarity	NPC229190
0.9108	High Similarity	NPC173137
0.9108	High Similarity	NPC3629
0.9103	High Similarity	NPC311574
0.9103	High Similarity	NPC264932
0.9103	High Similarity	NPC123544
0.9085	High Similarity	NPC328740
0.9085	High Similarity	NPC472580
0.9085	High Similarity	NPC477897
0.9085	High Similarity	NPC289774
0.9085	High Similarity	NPC209846
0.9085	High Similarity	NPC471675
0.9079	High Similarity	NPC472628
0.9079	High Similarity	NPC471114
0.9073	High Similarity	NPC211466
0.9073	High Similarity	NPC14001
0.9073	High Similarity	NPC296998
0.9073	High Similarity	NPC40086
0.9073	High Similarity	NPC166757
0.9073	High Similarity	NPC3779
0.9073	High Similarity	NPC122828
0.9073	High Similarity	NPC476182
0.9073	High Similarity	NPC176869
0.9073	High Similarity	NPC472627
0.9073	High Similarity	NPC473077
0.9073	High Similarity	NPC44721
0.9068	High Similarity	NPC8704
0.9068	High Similarity	NPC287884
0.9067	High Similarity	NPC216538
0.9067	High Similarity	NPC271288
0.9067	High Similarity	NPC273538
0.9067	High Similarity	NPC311144
0.9057	High Similarity	NPC224280
0.9057	High Similarity	NPC234052
0.9051	High Similarity	NPC52204
0.9051	High Similarity	NPC259834
0.9051	High Similarity	NPC472402
0.9051	High Similarity	NPC474150
0.9051	High Similarity	NPC474162
0.9045	High Similarity	NPC172687
0.9038	High Similarity	NPC161650
0.9038	High Similarity	NPC210048
0.9038	High Similarity	NPC471209
0.9032	High Similarity	NPC275575
0.9032	High Similarity	NPC470681
0.9026	High Similarity	NPC327269
0.9026	High Similarity	NPC477957
0.9026	High Similarity	NPC31627
0.9026	High Similarity	NPC476238
0.902	High Similarity	NPC472633
0.902	High Similarity	NPC472421
0.902	High Similarity	NPC61258
0.9013	High Similarity	NPC266572
0.9013	High Similarity	NPC161191
0.9007	High Similarity	NPC306488
0.9007	High Similarity	NPC20488
0.9007	High Similarity	NPC477955
0.9007	High Similarity	NPC246948
0.9007	High Similarity	NPC5820
0.9007	High Similarity	NPC83357
0.9007	High Similarity	NPC88964
0.9007	High Similarity	NPC299011
0.9007	High Similarity	NPC267375
0.9007	High Similarity	NPC214774
0.9007	High Similarity	NPC54577
0.9007	High Similarity	NPC111786
0.9007	High Similarity	NPC301276
0.9007	High Similarity	NPC470647
0.9007	High Similarity	NPC195621
0.9007	High Similarity	NPC312973
0.9007	High Similarity	NPC472629
0.9007	High Similarity	NPC67805
0.9007	High Similarity	NPC176229
0.9007	High Similarity	NPC475052
0.9007	High Similarity	NPC142405
0.9007	High Similarity	NPC220418
0.9007	High Similarity	NPC178343
0.9006	High Similarity	NPC152477
0.9006	High Similarity	NPC242395
0.9	High Similarity	NPC24821
0.9	High Similarity	NPC113770
0.9	High Similarity	NPC212932
0.9	High Similarity	NPC219915
0.9	High Similarity	NPC9117
0.9	High Similarity	NPC316816
0.9	High Similarity	NPC120593
0.9	High Similarity	NPC106985
0.9	High Similarity	NPC190637
0.9	High Similarity	NPC478086
0.9	High Similarity	NPC82330
0.9	High Similarity	NPC166138
0.9	High Similarity	NPC214166
0.9	High Similarity	NPC471213
0.9	High Similarity	NPC293053
0.9	High Similarity	NPC18585
0.8994	High Similarity	NPC146134
0.8994	High Similarity	NPC183672
0.8994	High Similarity	NPC41301
0.8994	High Similarity	NPC472581
0.8994	High Similarity	NPC472625
0.8987	High Similarity	NPC472632
0.8987	High Similarity	NPC134783
0.8987	High Similarity	NPC471210
0.8981	High Similarity	NPC152904
0.8981	High Similarity	NPC125969
0.8981	High Similarity	NPC55738
0.8981	High Similarity	NPC295090
0.8981	High Similarity	NPC22192
0.8981	High Similarity	NPC473990
0.8974	High Similarity	NPC208152
0.8974	High Similarity	NPC470600
0.8974	High Similarity	NPC69531
0.8974	High Similarity	NPC78492
0.8961	High Similarity	NPC474744
0.8961	High Similarity	NPC474772
0.8961	High Similarity	NPC472423
0.8961	High Similarity	NPC325429
0.8954	High Similarity	NPC470461

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 NPC146636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	928
0.2-0.3	1706
0.3-0.4	2620
0.4-0.5	1854
0.5-0.6	1066
0.6-0.7	423
0.7-0.8	152
0.8-0.85	28
0.85-0.9	21
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9067	High Similarity	NPD4378	Clinical (unspecified phase)
0.8917	High Similarity	NPD7075	Discontinued
0.8896	High Similarity	NPD4380	Phase 2
0.8889	High Similarity	NPD7804	Clinical (unspecified phase)
0.8846	High Similarity	NPD7096	Clinical (unspecified phase)
0.8846	High Similarity	NPD2393	Clinical (unspecified phase)
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.8671	High Similarity	NPD8443	Clinical (unspecified phase)
0.8662	High Similarity	NPD6801	Discontinued
0.8662	High Similarity	NPD1934	Approved
0.8634	High Similarity	NPD6959	Discontinued
0.86	High Similarity	NPD1550	Clinical (unspecified phase)
0.86	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD7410	Clinical (unspecified phase)
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8543	High Similarity	NPD1549	Phase 2
0.8506	High Similarity	NPD6799	Approved
0.85	High Similarity	NPD3882	Suspended
0.8494	Intermediate Similarity	NPD7074	Phase 3
0.8491	Intermediate Similarity	NPD2801	Approved
0.8481	Intermediate Similarity	NPD7411	Suspended
0.8457	Intermediate Similarity	NPD5494	Approved
0.8443	Intermediate Similarity	NPD6797	Phase 2
0.8418	Intermediate Similarity	NPD6599	Discontinued
0.8397	Intermediate Similarity	NPD1512	Approved
0.8393	Intermediate Similarity	NPD7251	Discontinued
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8364	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8343	Intermediate Similarity	NPD7808	Phase 3
0.8323	Intermediate Similarity	NPD7054	Approved
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8289	Intermediate Similarity	NPD2796	Approved
0.8274	Intermediate Similarity	NPD7472	Approved
0.8269	Intermediate Similarity	NPD1511	Approved
0.8247	Intermediate Similarity	NPD2800	Approved
0.82	Intermediate Similarity	NPD1240	Approved
0.816	Intermediate Similarity	NPD7768	Phase 2
0.816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD5403	Approved
0.811	Intermediate Similarity	NPD3749	Approved
0.8098	Intermediate Similarity	NPD5402	Approved
0.8092	Intermediate Similarity	NPD1607	Approved
0.8047	Intermediate Similarity	NPD3818	Discontinued
0.8024	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD5401	Approved
0.7966	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7962	Intermediate Similarity	NPD3750	Approved
0.7927	Intermediate Similarity	NPD1465	Phase 2
0.7898	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5844	Phase 1
0.7888	Intermediate Similarity	NPD920	Approved
0.7875	Intermediate Similarity	NPD2532	Approved
0.7875	Intermediate Similarity	NPD2534	Approved
0.7875	Intermediate Similarity	NPD2533	Approved
0.7836	Intermediate Similarity	NPD3751	Discontinued
0.7829	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3787	Discontinued
0.7791	Intermediate Similarity	NPD7286	Phase 2
0.7756	Intermediate Similarity	NPD2799	Discontinued
0.7751	Intermediate Similarity	NPD1247	Approved
0.7742	Intermediate Similarity	NPD6651	Approved
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7722	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7701	Intermediate Similarity	NPD5953	Discontinued
0.7697	Intermediate Similarity	NPD4908	Phase 1
0.767	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD8312	Approved
0.7663	Intermediate Similarity	NPD6779	Approved
0.7663	Intermediate Similarity	NPD6780	Approved
0.7663	Intermediate Similarity	NPD6782	Approved
0.7663	Intermediate Similarity	NPD6777	Approved
0.7663	Intermediate Similarity	NPD6781	Approved
0.7663	Intermediate Similarity	NPD6776	Approved
0.7663	Intermediate Similarity	NPD6778	Approved
0.7661	Intermediate Similarity	NPD3926	Phase 2
0.7658	Intermediate Similarity	NPD2344	Approved
0.7654	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3748	Approved
0.7633	Intermediate Similarity	NPD919	Approved
0.7597	Intermediate Similarity	NPD2313	Discontinued
0.7596	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6099	Approved
0.7595	Intermediate Similarity	NPD6100	Approved
0.7593	Intermediate Similarity	NPD7390	Discontinued
0.7582	Intermediate Similarity	NPD4360	Phase 2
0.7582	Intermediate Similarity	NPD4363	Phase 3
0.7576	Intermediate Similarity	NPD3226	Approved
0.7562	Intermediate Similarity	NPD1243	Approved
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7542	Intermediate Similarity	NPD8150	Discontinued
0.754	Intermediate Similarity	NPD7697	Approved
0.754	Intermediate Similarity	NPD7696	Phase 3
0.754	Intermediate Similarity	NPD7698	Approved
0.754	Intermediate Similarity	NPD7435	Discontinued
0.7532	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.747	Intermediate Similarity	NPD7458	Discontinued
0.7469	Intermediate Similarity	NPD2309	Approved
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7448	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7783	Phase 2
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7421	Intermediate Similarity	NPD7584	Approved
0.7407	Intermediate Similarity	NPD7871	Phase 2
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7870	Phase 2
0.7399	Intermediate Similarity	NPD5711	Approved
0.7399	Intermediate Similarity	NPD5710	Approved
0.7391	Intermediate Similarity	NPD2424	Discontinued
0.7391	Intermediate Similarity	NPD6535	Approved
0.7391	Intermediate Similarity	NPD6534	Approved
0.7389	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1613	Approved
0.7389	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6798	Discontinued
0.7366	Intermediate Similarity	NPD7700	Phase 2
0.7366	Intermediate Similarity	NPD7699	Phase 2
0.7363	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8151	Discontinued
0.7342	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD5124	Phase 1
0.7316	Intermediate Similarity	NPD8320	Phase 1
0.7316	Intermediate Similarity	NPD8319	Approved
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7312	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4625	Phase 3
0.7306	Intermediate Similarity	NPD7874	Approved
0.7306	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD1203	Approved
0.7268	Intermediate Similarity	NPD7801	Approved
0.7261	Intermediate Similarity	NPD3268	Approved
0.7258	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4361	Phase 2
0.7257	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7233	Intermediate Similarity	NPD230	Phase 1
0.7232	Intermediate Similarity	NPD7228	Approved
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7215	Intermediate Similarity	NPD6233	Phase 2
0.7211	Intermediate Similarity	NPD6823	Phase 2
0.72	Intermediate Similarity	NPD7229	Phase 3
0.72	Intermediate Similarity	NPD1548	Phase 1
0.7186	Intermediate Similarity	NPD5049	Phase 3
0.7174	Intermediate Similarity	NPD4287	Approved
0.7161	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD2354	Approved
0.7151	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7125	Intermediate Similarity	NPD1933	Approved
0.7125	Intermediate Similarity	NPD447	Suspended
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3823	Discontinued
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7091	Intermediate Similarity	NPD7003	Approved
0.7089	Intermediate Similarity	NPD3027	Phase 3
0.7078	Intermediate Similarity	NPD9717	Approved
0.7052	Intermediate Similarity	NPD4288	Approved
0.7048	Intermediate Similarity	NPD3887	Approved
0.7044	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD7097	Phase 1
0.7035	Intermediate Similarity	NPD6844	Discontinued
0.7035	Intermediate Similarity	NPD37	Approved
0.7032	Intermediate Similarity	NPD4749	Approved
0.703	Intermediate Similarity	NPD1652	Phase 2
0.703	Intermediate Similarity	NPD2654	Approved
0.7026	Intermediate Similarity	NPD7585	Approved
0.7024	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD422	Phase 1

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