NPASS Compound

Structure

NPC41301 OpenBabel07101718222D 30 32 0 0 1 0 0 0 0 0999 V2000 -4.7603 -2.3108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5355 -3.5355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 -1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 2.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0872 -1.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 -0.8966 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 1.2247 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 -3.7944 -2.5696 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 -2.6390 -0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 0.2588 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 -2.1907 1.4836 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 -1.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 0.7765 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 1 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4495 2.4495 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 0.1305 -0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 -1.4142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8637 1.0353 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 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 17 2 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 22 1 0 0 0 0 10 30 1 0 0 0 0 12 23 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 0 0 0 0 15 18 2 0 0 0 0 15 24 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 30 1 0 0 0 0 18 21 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 26 2 0 0 0 0 22 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.15
Volume:	412.629
LogP:	3.578
LogD:	2.937
LogS:	-3.574
# Rotatable Bonds:	5
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.548
Synthetic Accessibility Score:	3.716
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.012
MDCK Permeability:	7.596529485454084e-06
Pgp-inhibitor:	0.038
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.82
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	91.05525207519531%
Volume Distribution (VD):	1.027
Pgp-substrate:	10.035971641540527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.868
CYP2C19-inhibitor:	0.54
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.565
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.722
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.639
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	13.613
Half-life (T1/2):	0.42

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.214
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.851
Skin Sensitization:	0.815
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.402
Respiratory Toxicity:	0.255

Download Data

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

Natural Product: NPC41301

Natural Product ID:	NPC41301
*Common Name:**	Sophonorol D
IUPAC Name:	(3S)-3,5,7-trihydroxy-3-[5-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-enyl)phenyl]-2H-chromen-4-one
Synonyms:	Sophonorol D
Standard InCHIKey:	ZXYPRXHIKNCGTA-JOCHJYFZSA-N
Standard InCHI:	InChI=1S/C22H24O8/c1-11(2)5-6-13-19(28-3)14(9-16(25)20(13)29-4)22(27)10-30-17-8-12(23)7-15(24)18(17)21(22)26/h5,7-9,23-25,27H,6,10H2,1-4H3/t22-/m1/s1
SMILES:	COc1c(CC=C(C)C)c(OC)c(cc1[C@]1(O)COc2c(C1=O)c(O)cc(c2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL549957
PubChem CID:	44233681
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003525] 3'-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	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	IC50	=	171700.0	nM	PMID[511903]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	105600.0	nM	PMID[511903]
NPT2	Others	Unspecified		Ratio IC50	=	2.0	n.a.	PMID[511903]

☑ 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 NPC41301 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	430
0.1-0.2	1714
0.2-0.3	4298
0.3-0.4	10217
0.4-0.5	7775
0.5-0.6	3620
0.6-0.7	4839
0.7-0.8	5360
0.8-0.85	2583
0.85-0.9	1372
0.9-0.95	476
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC470459
0.9615	High Similarity	NPC61010
0.9615	High Similarity	NPC266314
0.9613	High Similarity	NPC152904
0.956	High Similarity	NPC158761
0.9557	High Similarity	NPC224280
0.9557	High Similarity	NPC62261
0.9557	High Similarity	NPC470457
0.9551	High Similarity	NPC228785
0.9551	High Similarity	NPC14353
0.9551	High Similarity	NPC56085
0.9551	High Similarity	NPC246478
0.9551	High Similarity	NPC470326
0.9548	High Similarity	NPC262286
0.9548	High Similarity	NPC36852
0.9548	High Similarity	NPC78225
0.9548	High Similarity	NPC223787
0.9548	High Similarity	NPC469584
0.95	High Similarity	NPC326877
0.95	High Similarity	NPC177480
0.9497	High Similarity	NPC170245
0.9497	High Similarity	NPC470462
0.9494	High Similarity	NPC236521
0.9494	High Similarity	NPC152659
0.9494	High Similarity	NPC248638
0.9494	High Similarity	NPC7483
0.949	High Similarity	NPC471499
0.949	High Similarity	NPC278052
0.949	High Similarity	NPC40491
0.9487	High Similarity	NPC100123
0.9487	High Similarity	NPC250214
0.9487	High Similarity	NPC55738
0.9487	High Similarity	NPC95936
0.9487	High Similarity	NPC476242
0.9484	High Similarity	NPC191146
0.9484	High Similarity	NPC68093
0.9484	High Similarity	NPC303255
0.9484	High Similarity	NPC474520
0.9484	High Similarity	NPC138243
0.9437	High Similarity	NPC117854
0.9437	High Similarity	NPC6588
0.9437	High Similarity	NPC470456
0.9437	High Similarity	NPC477154
0.9434	High Similarity	NPC326520
0.9434	High Similarity	NPC234052
0.9434	High Similarity	NPC275780
0.9434	High Similarity	NPC239752
0.9434	High Similarity	NPC472450
0.943	High Similarity	NPC472448
0.943	High Similarity	NPC474162
0.943	High Similarity	NPC474150
0.943	High Similarity	NPC83922
0.943	High Similarity	NPC25152
0.9427	High Similarity	NPC287328
0.9427	High Similarity	NPC476980
0.9427	High Similarity	NPC475886
0.9427	High Similarity	NPC472630
0.9427	High Similarity	NPC320359
0.9427	High Similarity	NPC204290
0.9427	High Similarity	NPC472631
0.9427	High Similarity	NPC282009
0.9427	High Similarity	NPC263449
0.9427	High Similarity	NPC474287
0.9423	High Similarity	NPC156057
0.9423	High Similarity	NPC96167
0.9423	High Similarity	NPC93376
0.9423	High Similarity	NPC162869
0.9423	High Similarity	NPC78302
0.9423	High Similarity	NPC189179
0.9423	High Similarity	NPC245758
0.9423	High Similarity	NPC75215
0.9423	High Similarity	NPC472438
0.9423	High Similarity	NPC235215
0.9423	High Similarity	NPC165977
0.9423	High Similarity	NPC474208
0.9423	High Similarity	NPC27337
0.9423	High Similarity	NPC474836
0.9423	High Similarity	NPC29841
0.9423	High Similarity	NPC475267
0.9423	High Similarity	NPC7973
0.9423	High Similarity	NPC217677
0.9423	High Similarity	NPC472911
0.9423	High Similarity	NPC300727
0.9423	High Similarity	NPC472910
0.9423	High Similarity	NPC67876
0.9423	High Similarity	NPC222814
0.9423	High Similarity	NPC472913
0.9423	High Similarity	NPC48208
0.9423	High Similarity	NPC227192
0.9423	High Similarity	NPC472914
0.9423	High Similarity	NPC224137
0.9423	High Similarity	NPC241904
0.9419	High Similarity	NPC113906
0.9419	High Similarity	NPC45849
0.9419	High Similarity	NPC200761
0.9419	High Similarity	NPC470327
0.9419	High Similarity	NPC477503
0.9383	High Similarity	NPC121333
0.9379	High Similarity	NPC242395
0.9379	High Similarity	NPC152477
0.9375	High Similarity	NPC39091
0.9375	High Similarity	NPC471213
0.9371	High Similarity	NPC472625
0.9371	High Similarity	NPC189473
0.9371	High Similarity	NPC220313
0.9371	High Similarity	NPC23298
0.9371	High Similarity	NPC475985
0.9371	High Similarity	NPC236132
0.9367	High Similarity	NPC308992
0.9367	High Similarity	NPC474351
0.9367	High Similarity	NPC173137
0.9367	High Similarity	NPC474186
0.9367	High Similarity	NPC471211
0.9367	High Similarity	NPC29876
0.9367	High Similarity	NPC134783
0.9367	High Similarity	NPC167678
0.9367	High Similarity	NPC475883
0.9367	High Similarity	NPC471212
0.9367	High Similarity	NPC474187
0.9367	High Similarity	NPC472634
0.9363	High Similarity	NPC130894
0.9363	High Similarity	NPC7846
0.9363	High Similarity	NPC300943
0.9363	High Similarity	NPC191459
0.9363	High Similarity	NPC22192
0.9363	High Similarity	NPC4481
0.9363	High Similarity	NPC115798
0.9363	High Similarity	NPC204854
0.9363	High Similarity	NPC261004
0.9363	High Similarity	NPC19687
0.9363	High Similarity	NPC105242
0.9363	High Similarity	NPC9609
0.9363	High Similarity	NPC288669
0.9363	High Similarity	NPC152166
0.9363	High Similarity	NPC22472
0.9363	High Similarity	NPC18772
0.9363	High Similarity	NPC18607
0.9363	High Similarity	NPC25495
0.9363	High Similarity	NPC143828
0.9363	High Similarity	NPC176300
0.9363	High Similarity	NPC253634
0.9359	High Similarity	NPC209614
0.9359	High Similarity	NPC278778
0.9359	High Similarity	NPC472916
0.9359	High Similarity	NPC98661
0.9359	High Similarity	NPC200388
0.9359	High Similarity	NPC55619
0.9359	High Similarity	NPC474638
0.9359	High Similarity	NPC268161
0.9359	High Similarity	NPC247017
0.9359	High Similarity	NPC100916
0.9359	High Similarity	NPC291878
0.9359	High Similarity	NPC49824
0.9359	High Similarity	NPC470328
0.9359	High Similarity	NPC255106
0.9359	High Similarity	NPC472626
0.9359	High Similarity	NPC195796
0.9359	High Similarity	NPC274730
0.9359	High Similarity	NPC235165
0.9359	High Similarity	NPC35038
0.9359	High Similarity	NPC142339
0.9359	High Similarity	NPC250922
0.9355	High Similarity	NPC74924
0.9355	High Similarity	NPC250822
0.9355	High Similarity	NPC75279
0.9355	High Similarity	NPC276409
0.9321	High Similarity	NPC74559
0.9317	High Similarity	NPC8965
0.9313	High Similarity	NPC50960
0.9313	High Similarity	NPC475888
0.9308	High Similarity	NPC472635
0.9308	High Similarity	NPC229632
0.9308	High Similarity	NPC211107
0.9308	High Similarity	NPC261470
0.9308	High Similarity	NPC81679
0.9308	High Similarity	NPC220912
0.9304	High Similarity	NPC174953
0.9304	High Similarity	NPC192686
0.9304	High Similarity	NPC472624
0.9304	High Similarity	NPC200746
0.9304	High Similarity	NPC470183
0.9304	High Similarity	NPC119209
0.9304	High Similarity	NPC36217
0.9304	High Similarity	NPC118256
0.9299	High Similarity	NPC99597
0.9299	High Similarity	NPC476981
0.9299	High Similarity	NPC299520
0.9299	High Similarity	NPC110070
0.9299	High Similarity	NPC203891
0.9299	High Similarity	NPC52889
0.9299	High Similarity	NPC471515
0.9299	High Similarity	NPC474055
0.9299	High Similarity	NPC101830
0.9299	High Similarity	NPC129684
0.9299	High Similarity	NPC236796
0.9299	High Similarity	NPC471479
0.9299	High Similarity	NPC163524
0.9299	High Similarity	NPC181960
0.9299	High Similarity	NPC305663
0.9299	High Similarity	NPC176665

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 NPC41301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	981
0.2-0.3	1940
0.3-0.4	2584
0.4-0.5	1727
0.5-0.6	931
0.6-0.7	429
0.7-0.8	132
0.8-0.85	28
0.85-0.9	11
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD2393	Clinical (unspecified phase)
0.9231	High Similarity	NPD2801	Approved
0.9167	High Similarity	NPD1934	Approved
0.9074	High Similarity	NPD6166	Phase 2
0.9074	High Similarity	NPD6168	Clinical (unspecified phase)
0.9074	High Similarity	NPD6167	Clinical (unspecified phase)
0.8994	High Similarity	NPD3882	Suspended
0.8827	High Similarity	NPD5494	Approved
0.8812	High Similarity	NPD3817	Phase 2
0.881	High Similarity	NPD4338	Clinical (unspecified phase)
0.8782	High Similarity	NPD1512	Approved
0.8718	High Similarity	NPD4378	Clinical (unspecified phase)
0.8704	High Similarity	NPD7075	Discontinued
0.8654	High Similarity	NPD1511	Approved
0.8642	High Similarity	NPD4868	Clinical (unspecified phase)
0.8631	High Similarity	NPD7074	Phase 3
0.8623	High Similarity	NPD3818	Discontinued
0.858	High Similarity	NPD6797	Phase 2
0.8571	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD4380	Phase 2
0.8529	High Similarity	NPD7251	Discontinued
0.8521	High Similarity	NPD7472	Approved
0.8519	High Similarity	NPD7096	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6232	Discontinued
0.848	Intermediate Similarity	NPD7808	Phase 3
0.8452	Intermediate Similarity	NPD7473	Discontinued
0.8405	Intermediate Similarity	NPD7819	Suspended
0.8363	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD5844	Phase 1
0.8353	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD1247	Approved
0.8323	Intermediate Similarity	NPD6959	Discontinued
0.8293	Intermediate Similarity	NPD1465	Phase 2
0.8269	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5402	Approved
0.8217	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD7411	Suspended
0.8118	Intermediate Similarity	NPD3926	Phase 2
0.811	Intermediate Similarity	NPD6599	Discontinued
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD919	Approved
0.7975	Intermediate Similarity	NPD2796	Approved
0.7965	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2800	Approved
0.7921	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2533	Approved
0.7914	Intermediate Similarity	NPD2534	Approved
0.7914	Intermediate Similarity	NPD2532	Approved
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD943	Approved
0.7885	Intermediate Similarity	NPD1240	Approved
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7818	Intermediate Similarity	NPD5403	Approved
0.7796	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7771	Intermediate Similarity	NPD3751	Discontinued
0.7771	Intermediate Similarity	NPD1613	Approved
0.7771	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7768	Phase 2
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6190	Approved
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7719	Intermediate Similarity	NPD3749	Approved
0.7701	Intermediate Similarity	NPD6782	Approved
0.7701	Intermediate Similarity	NPD6778	Approved
0.7701	Intermediate Similarity	NPD6776	Approved
0.7701	Intermediate Similarity	NPD6781	Approved
0.7701	Intermediate Similarity	NPD6777	Approved
0.7701	Intermediate Similarity	NPD6779	Approved
0.7701	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6780	Approved
0.7697	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6100	Approved
0.764	Intermediate Similarity	NPD6099	Approved
0.7619	Intermediate Similarity	NPD3226	Approved
0.7607	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD37	Approved
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.7582	Intermediate Similarity	NPD8434	Phase 2
0.758	Intermediate Similarity	NPD3027	Phase 3
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7578	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7228	Approved
0.7562	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD3750	Approved
0.756	Intermediate Similarity	NPD1653	Approved
0.7558	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD4966	Approved
0.7558	Intermediate Similarity	NPD4965	Approved
0.7542	Intermediate Similarity	NPD5953	Discontinued
0.753	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD920	Approved
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7698	Approved
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2346	Discontinued
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7459	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7870	Phase 2
0.7448	Intermediate Similarity	NPD7871	Phase 2
0.7443	Intermediate Similarity	NPD5710	Approved
0.7443	Intermediate Similarity	NPD5711	Approved
0.7433	Intermediate Similarity	NPD6534	Approved
0.7433	Intermediate Similarity	NPD6535	Approved
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7423	Intermediate Similarity	NPD7701	Phase 2
0.7423	Intermediate Similarity	NPD1551	Phase 2
0.7421	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8313	Approved
0.7418	Intermediate Similarity	NPD8312	Approved
0.7403	Intermediate Similarity	NPD7685	Pre-registration
0.7394	Intermediate Similarity	NPD1243	Approved
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2344	Approved
0.736	Intermediate Similarity	NPD2403	Approved
0.7354	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7874	Approved
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD9494	Approved
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7699	Phase 2
0.7316	Intermediate Similarity	NPD7700	Phase 2
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.731	Intermediate Similarity	NPD7801	Approved
0.731	Intermediate Similarity	NPD7783	Phase 2
0.731	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.7284	Intermediate Similarity	NPD1933	Approved
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3748	Approved
0.7254	Intermediate Similarity	NPD6823	Phase 2
0.725	Intermediate Similarity	NPD4625	Phase 3
0.7249	Intermediate Similarity	NPD4363	Phase 3
0.7249	Intermediate Similarity	NPD4360	Phase 2
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7207	Intermediate Similarity	NPD5242	Approved
0.7202	Intermediate Similarity	NPD2309	Approved
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7584	Approved
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.716	Intermediate Similarity	NPD6233	Phase 2
0.7157	Intermediate Similarity	NPD7907	Approved
0.7151	Intermediate Similarity	NPD7229	Phase 3
0.7126	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2424	Discontinued
0.7125	Intermediate Similarity	NPD2861	Phase 2
0.712	Intermediate Similarity	NPD7240	Approved
0.7113	Intermediate Similarity	NPD2494	Approved
0.7113	Intermediate Similarity	NPD2493	Approved
0.7102	Intermediate Similarity	NPD5353	Approved
0.7099	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6798	Discontinued
0.7089	Intermediate Similarity	NPD4749	Approved
0.7086	Intermediate Similarity	NPD6844	Discontinued
0.7081	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD7549	Discontinued
0.7076	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.707	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD4665	Approved
0.7048	Intermediate Similarity	NPD7033	Discontinued
0.7045	Intermediate Similarity	NPD8455	Phase 2
0.7031	Intermediate Similarity	NPD4361	Phase 2
0.7031	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3452	Approved
0.7026	Intermediate Similarity	NPD3450	Approved
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7011	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7458	Discontinued
0.7005	Intermediate Similarity	NPD8319	Approved
0.7005	Intermediate Similarity	NPD8320	Phase 1
0.7005	Intermediate Similarity	NPD4583	Approved
0.7005	Intermediate Similarity	NPD4582	Approved
0.7	Intermediate Similarity	NPD1203	Approved
0.6994	Remote Similarity	NPD3268	Approved
0.699	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7211	Clinical (unspecified phase)

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