NPASS Compound

Structure

NPC260979 OpenBabel07101718182D 22 24 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 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 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 -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 -2.0000 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 1.7321 1.0000 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 1 0 0 0 0 7 22 1 0 0 0 0 9 17 1 0 0 0 0 10 8 1 6 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 16 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	2.315
LogD:	2.272
LogS:	-3.818
# Rotatable Bonds:	2
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.787
Synthetic Accessibility Score:	2.987
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.842
MDCK Permeability:	8.984296073322184e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.713
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	97.84066772460938%
Volume Distribution (VD):	0.496
Pgp-substrate:	2.3522608280181885%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.433
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.711
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.611
CYP2D6-substrate:	0.848
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	12.875
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.627
AMES Toxicity:	0.483
Rat Oral Acute Toxicity:	0.434
Maximum Recommended Daily Dose:	0.194
Skin Sensitization:	0.867
Carcinogencity:	0.158
Eye Corrosion:	0.003
Eye Irritation:	0.839
Respiratory Toxicity:	0.118

Download Data

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

Natural Product: NPC260979

Natural Product ID:	NPC260979
*Common Name:**	(3S)-Secundiflorol H
IUPAC Name:	(3S)-5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	(3S)-Secundiflorol H
Standard InCHIKey:	VCQMNUJRSNCWDM-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-6,10,17-19H,7H2,1H3/t10-/m1/s1
SMILES:	COc1ccc(cc1O)[C@H]1COc2c(C1=O)c(O)cc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088033
PubChem CID:	46881083
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO14114	Dalbergia parviflora	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[510937]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	1.3	uM	PMID[510937]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	2.7	uM	PMID[510937]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.6	uM	PMID[510937]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	5.7	uM	PMID[510937]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.5	uM	PMID[510937]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[510937]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	2.9	uM	PMID[510937]

☑ 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 NPC260979 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	396
0.1-0.2	1580
0.2-0.3	4058
0.3-0.4	10207
0.4-0.5	7894
0.5-0.6	3264
0.6-0.7	4752
0.7-0.8	5586
0.8-0.85	2772
0.85-0.9	1650
0.9-0.95	468
0.95-1	70

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC469550
0.9863	High Similarity	NPC472912
0.9732	High Similarity	NPC129684
0.9732	High Similarity	NPC299520
0.9728	High Similarity	NPC302950
0.9728	High Similarity	NPC219582
0.9728	High Similarity	NPC236637
0.9724	High Similarity	NPC3036
0.9662	High Similarity	NPC18727
0.966	High Similarity	NPC31363
0.9658	High Similarity	NPC105512
0.96	High Similarity	NPC472911
0.96	High Similarity	NPC245758
0.96	High Similarity	NPC472914
0.96	High Similarity	NPC469584
0.96	High Similarity	NPC472910
0.96	High Similarity	NPC472913
0.96	High Similarity	NPC222814
0.96	High Similarity	NPC96167
0.9597	High Similarity	NPC255807
0.9597	High Similarity	NPC31018
0.9595	High Similarity	NPC477231
0.9595	High Similarity	NPC257648
0.9592	High Similarity	NPC29231
0.9536	High Similarity	NPC55738
0.9533	High Similarity	NPC326037
0.9533	High Similarity	NPC278778
0.9533	High Similarity	NPC255106
0.9533	High Similarity	NPC235165
0.9533	High Similarity	NPC291878
0.9533	High Similarity	NPC195796
0.9533	High Similarity	NPC320825
0.9533	High Similarity	NPC35038
0.9533	High Similarity	NPC13858
0.9524	High Similarity	NPC223579
0.9524	High Similarity	NPC183950
0.9524	High Similarity	NPC52005
0.9524	High Similarity	NPC137062
0.9524	High Similarity	NPC287101
0.9521	High Similarity	NPC95864
0.9477	High Similarity	NPC474162
0.9477	High Similarity	NPC474150
0.9474	High Similarity	NPC474960
0.9474	High Similarity	NPC36217
0.947	High Similarity	NPC27337
0.947	High Similarity	NPC210084
0.947	High Similarity	NPC475267
0.947	High Similarity	NPC67876
0.947	High Similarity	NPC156057
0.947	High Similarity	NPC474208
0.947	High Similarity	NPC474055
0.947	High Similarity	NPC52530
0.947	High Similarity	NPC474836
0.947	High Similarity	NPC162869
0.947	High Similarity	NPC181960
0.947	High Similarity	NPC472963
0.947	High Similarity	NPC99597
0.947	High Similarity	NPC472598
0.947	High Similarity	NPC471479
0.947	High Similarity	NPC111969
0.947	High Similarity	NPC291508
0.947	High Similarity	NPC48208
0.947	High Similarity	NPC471515
0.9467	High Similarity	NPC45849
0.9467	High Similarity	NPC200761
0.9467	High Similarity	NPC472909
0.9467	High Similarity	NPC57674
0.9467	High Similarity	NPC152951
0.9467	High Similarity	NPC67396
0.9467	High Similarity	NPC168247
0.9467	High Similarity	NPC470327
0.9467	High Similarity	NPC477503
0.9467	High Similarity	NPC117992
0.9467	High Similarity	NPC230149
0.9467	High Similarity	NPC2928
0.9463	High Similarity	NPC199100
0.9463	High Similarity	NPC180234
0.9463	High Similarity	NPC120537
0.9459	High Similarity	NPC151473
0.9459	High Similarity	NPC338131
0.9456	High Similarity	NPC321011
0.9456	High Similarity	NPC120464
0.9456	High Similarity	NPC196277
0.9456	High Similarity	NPC194653
0.9456	High Similarity	NPC203747
0.9456	High Similarity	NPC188679
0.9456	High Similarity	NPC80710
0.9456	High Similarity	NPC43669
0.9456	High Similarity	NPC294852
0.9456	High Similarity	NPC272721
0.9456	High Similarity	NPC139364
0.9456	High Similarity	NPC254702
0.9412	High Similarity	NPC266314
0.9412	High Similarity	NPC173137
0.9404	High Similarity	NPC472626
0.9404	High Similarity	NPC474638
0.9404	High Similarity	NPC470328
0.9404	High Similarity	NPC24640
0.9404	High Similarity	NPC472907
0.9404	High Similarity	NPC209614
0.9404	High Similarity	NPC250922
0.9404	High Similarity	NPC471500
0.9404	High Similarity	NPC472916
0.94	High Similarity	NPC33051
0.94	High Similarity	NPC292214
0.94	High Similarity	NPC167091
0.94	High Similarity	NPC472905
0.94	High Similarity	NPC271779
0.94	High Similarity	NPC227337
0.94	High Similarity	NPC273462
0.94	High Similarity	NPC192083
0.94	High Similarity	NPC141212
0.94	High Similarity	NPC88645
0.94	High Similarity	NPC213896
0.94	High Similarity	NPC49402
0.94	High Similarity	NPC70433
0.94	High Similarity	NPC206238
0.9396	High Similarity	NPC125062
0.9396	High Similarity	NPC252933
0.9396	High Similarity	NPC54394
0.9396	High Similarity	NPC117579
0.9396	High Similarity	NPC200740
0.9392	High Similarity	NPC139293
0.9392	High Similarity	NPC48479
0.9392	High Similarity	NPC195763
0.9392	High Similarity	NPC264289
0.9392	High Similarity	NPC200060
0.9392	High Similarity	NPC183959
0.9392	High Similarity	NPC333691
0.9392	High Similarity	NPC264550
0.9392	High Similarity	NPC69430
0.9392	High Similarity	NPC177298
0.9392	High Similarity	NPC40290
0.9392	High Similarity	NPC142876
0.9392	High Similarity	NPC1612
0.9388	High Similarity	NPC470511
0.9388	High Similarity	NPC12200
0.9388	High Similarity	NPC77378
0.9388	High Similarity	NPC108406
0.9351	High Similarity	NPC201800
0.9351	High Similarity	NPC472964
0.9346	High Similarity	NPC287328
0.9346	High Similarity	NPC472902
0.9346	High Similarity	NPC470183
0.9346	High Similarity	NPC192686
0.9346	High Similarity	NPC282009
0.9346	High Similarity	NPC472624
0.9346	High Similarity	NPC263449
0.9346	High Similarity	NPC118256
0.9346	High Similarity	NPC119209
0.9342	High Similarity	NPC52889
0.9342	High Similarity	NPC187745
0.9342	High Similarity	NPC180011
0.9342	High Similarity	NPC241904
0.9342	High Similarity	NPC161960
0.9342	High Similarity	NPC219867
0.9342	High Similarity	NPC78225
0.9342	High Similarity	NPC300727
0.9342	High Similarity	NPC304008
0.9342	High Similarity	NPC108456
0.9342	High Similarity	NPC223787
0.9342	High Similarity	NPC136674
0.9338	High Similarity	NPC37392
0.9338	High Similarity	NPC234255
0.9338	High Similarity	NPC226025
0.9338	High Similarity	NPC321779
0.9338	High Similarity	NPC213622
0.9338	High Similarity	NPC256925
0.9333	High Similarity	NPC60972
0.9333	High Similarity	NPC279989
0.9333	High Similarity	NPC57030
0.9333	High Similarity	NPC198826
0.9333	High Similarity	NPC246162
0.9333	High Similarity	NPC240476
0.9333	High Similarity	NPC55205
0.9333	High Similarity	NPC100887
0.9333	High Similarity	NPC212678
0.9333	High Similarity	NPC101996
0.9333	High Similarity	NPC61506
0.9333	High Similarity	NPC471982
0.9333	High Similarity	NPC131624
0.9333	High Similarity	NPC187498
0.9333	High Similarity	NPC25270
0.9333	High Similarity	NPC71334
0.9333	High Similarity	NPC156222
0.9333	High Similarity	NPC9743
0.9333	High Similarity	NPC36835
0.9333	High Similarity	NPC256283
0.9333	High Similarity	NPC106976
0.9333	High Similarity	NPC39007
0.9333	High Similarity	NPC241498
0.9333	High Similarity	NPC162313
0.9333	High Similarity	NPC188203
0.9333	High Similarity	NPC82325
0.9333	High Similarity	NPC120163
0.9333	High Similarity	NPC260491
0.9333	High Similarity	NPC293183
0.9333	High Similarity	NPC39732
0.9333	High Similarity	NPC83508
0.9333	High Similarity	NPC222830

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 NPC260979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	947
0.2-0.3	1669
0.3-0.4	2623
0.4-0.5	1768
0.5-0.6	1037
0.6-0.7	546
0.7-0.8	144
0.8-0.85	33
0.85-0.9	18
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9728	High Similarity	NPD1934	Approved
0.94	High Similarity	NPD2393	Clinical (unspecified phase)
0.9272	High Similarity	NPD2801	Approved
0.9184	High Similarity	NPD1511	Approved
0.915	High Similarity	NPD3882	Suspended
0.9108	High Similarity	NPD6166	Phase 2
0.9108	High Similarity	NPD6167	Clinical (unspecified phase)
0.9108	High Similarity	NPD6168	Clinical (unspecified phase)
0.906	High Similarity	NPD1512	Approved
0.8904	High Similarity	NPD1550	Clinical (unspecified phase)
0.8904	High Similarity	NPD1552	Clinical (unspecified phase)
0.8882	High Similarity	NPD7074	Phase 3
0.8844	High Similarity	NPD1549	Phase 2
0.8839	High Similarity	NPD3817	Phase 2
0.882	High Similarity	NPD7054	Approved
0.8765	High Similarity	NPD7472	Approved
0.8758	High Similarity	NPD3818	Discontinued
0.8734	High Similarity	NPD5494	Approved
0.8662	High Similarity	NPD4868	Clinical (unspecified phase)
0.8639	High Similarity	NPD1510	Phase 2
0.8618	High Similarity	NPD4378	Clinical (unspecified phase)
0.8608	High Similarity	NPD7075	Discontinued
0.8599	High Similarity	NPD8443	Clinical (unspecified phase)
0.8598	High Similarity	NPD6797	Phase 2
0.8581	High Similarity	NPD4380	Phase 2
0.8545	High Similarity	NPD7251	Discontinued
0.8535	High Similarity	NPD7819	Suspended
0.8535	High Similarity	NPD7096	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7808	Phase 3
0.8494	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1240	Approved
0.8491	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7473	Discontinued
0.8456	Intermediate Similarity	NPD2796	Approved
0.8431	Intermediate Similarity	NPD6799	Approved
0.8418	Intermediate Similarity	NPD1465	Phase 2
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8378	Intermediate Similarity	NPD1607	Approved
0.8367	Intermediate Similarity	NPD943	Approved
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD7411	Suspended
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8243	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1613	Approved
0.8239	Intermediate Similarity	NPD6801	Discontinued
0.8221	Intermediate Similarity	NPD6959	Discontinued
0.8219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3926	Phase 2
0.8117	Intermediate Similarity	NPD3750	Approved
0.8098	Intermediate Similarity	NPD919	Approved
0.8072	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD1247	Approved
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7974	Intermediate Similarity	NPD6100	Approved
0.7974	Intermediate Similarity	NPD6099	Approved
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7935	Intermediate Similarity	NPD2800	Approved
0.7925	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5403	Approved
0.7919	Intermediate Similarity	NPD3027	Phase 3
0.7914	Intermediate Similarity	NPD5402	Approved
0.7911	Intermediate Similarity	NPD5401	Approved
0.7904	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4628	Phase 3
0.7867	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1610	Phase 2
0.7852	Intermediate Similarity	NPD4908	Phase 1
0.7829	Intermediate Similarity	NPD447	Suspended
0.7829	Intermediate Similarity	NPD1933	Approved
0.7821	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2344	Approved
0.7799	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD2534	Approved
0.7799	Intermediate Similarity	NPD2532	Approved
0.7792	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3748	Approved
0.779	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD9494	Approved
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.7748	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2935	Discontinued
0.7736	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2799	Discontinued
0.7662	Intermediate Similarity	NPD6651	Approved
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2309	Approved
0.7607	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD1243	Approved
0.7593	Intermediate Similarity	NPD920	Approved
0.7584	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD37	Approved
0.7568	Intermediate Similarity	NPD1608	Approved
0.7562	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7228	Approved
0.7546	Intermediate Similarity	NPD1653	Approved
0.7545	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD4965	Approved
0.7533	Intermediate Similarity	NPD1203	Approved
0.7529	Intermediate Similarity	NPD5953	Discontinued
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD3268	Approved
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7483	Intermediate Similarity	NPD2798	Approved
0.7469	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7418	Intermediate Similarity	NPD4363	Phase 3
0.7418	Intermediate Similarity	NPD4360	Phase 2
0.7417	Intermediate Similarity	NPD2797	Approved
0.7414	Intermediate Similarity	NPD7286	Phase 2
0.7407	Intermediate Similarity	NPD7390	Discontinued
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2313	Discontinued
0.7401	Intermediate Similarity	NPD8313	Approved
0.7401	Intermediate Similarity	NPD8312	Approved
0.74	Intermediate Similarity	NPD4749	Approved
0.7391	Intermediate Similarity	NPD6190	Approved
0.7386	Intermediate Similarity	NPD6832	Phase 2
0.7384	Intermediate Similarity	NPD5242	Approved
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD17	Approved
0.7362	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD9717	Approved
0.7326	Intermediate Similarity	NPD5711	Approved
0.7326	Intermediate Similarity	NPD5710	Approved
0.732	Intermediate Similarity	NPD2861	Phase 2
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD3266	Approved
0.7303	Intermediate Similarity	NPD3267	Approved
0.729	Intermediate Similarity	NPD6798	Discontinued
0.729	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5353	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD1201	Approved
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7243	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2403	Approved
0.7235	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7225	Intermediate Similarity	NPD7229	Phase 3
0.7222	Intermediate Similarity	NPD4110	Phase 3
0.7222	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD9269	Phase 2
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7202	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1470	Approved
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.7179	Intermediate Similarity	NPD411	Approved
0.7176	Intermediate Similarity	NPD4288	Approved
0.7162	Intermediate Similarity	NPD5536	Phase 2
0.716	Intermediate Similarity	NPD2654	Approved
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7549	Discontinued
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7124	Intermediate Similarity	NPD3225	Approved
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD8166	Discontinued
0.7114	Intermediate Similarity	NPD9545	Approved
0.7105	Intermediate Similarity	NPD3972	Approved
0.7104	Intermediate Similarity	NPD4287	Approved
0.7103	Intermediate Similarity	NPD228	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7101	Intermediate Similarity	NPD6386	Approved
0.7098	Intermediate Similarity	NPD8151	Discontinued
0.7095	Intermediate Similarity	NPD7240	Approved
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7083	Intermediate Similarity	NPD7584	Approved
0.7076	Intermediate Similarity	NPD2296	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