NPASS Compound

Structure

CID5173 OpenBabel06191715322D 31 34 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 0.5000 1.8660 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 -0.8660 1.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 3 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 25 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 16 1 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 22 2 0 0 0 0 12 20 1 0 0 0 0 12 21 2 0 0 0 0 13 18 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 16 24 2 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 23 2 0 0 0 0 19 28 1 0 0 0 0 20 23 1 0 0 0 0 20 29 2 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 0 0 0 0 24 31 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	222.2
Volume:	268.877
LogP:	4.561
LogD:	3.981
LogS:	-4.139
# Rotatable Bonds:	7
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	3.452
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.517
MDCK Permeability:	2.2243115381570533e-05
Pgp-inhibitor:	0.659
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.16
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.363
Plasma Protein Binding (PPB):	97.36702728271484%
Volume Distribution (VD):	1.667
Pgp-substrate:	6.5568742752075195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.269
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.542
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.237
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.363
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.729
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	8.731
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.935
Carcinogencity:	0.045
Eye Corrosion:	0.438
Eye Irritation:	0.974
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC5173

Natural Product ID:	NPC5173
*Common Name:**	Yinyanghuo A
IUPAC Name:	5,7-dihydroxy-2-[8-(2-hydroxy-3-methylbut-3-enyl)-2,2-dimethylchromen-6-yl]chromen-4-one
Synonyms:
Standard InCHIKey:	ZAUWPDSVLSOCDG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O6/c1-13(2)18(27)9-16-8-15(7-14-5-6-25(3,4)31-24(14)16)21-12-20(29)23-19(28)10-17(26)11-22(23)30-21/h5-8,10-12,18,26-28H,1,9H2,2-4H3
SMILES:	Oc1cc(O)c2c(c1)oc(cc2=O)c1cc(CC(C(=C)C)O)c2c(c1)C=CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462969
PubChem CID:	5315393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003502] 3'-prenylated flavones

*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
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8699184]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	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
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	7140.0	nM	PMID[557117]

☑ 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 NPC5173 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	386
0.1-0.2	1524
0.2-0.3	3589
0.3-0.4	9105
0.4-0.5	9613
0.5-0.6	3710
0.6-0.7	5712
0.7-0.8	4453
0.8-0.85	2237
0.85-0.9	1638
0.9-0.95	675
0.95-1	55

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC6511
0.972	High Similarity	NPC296998
0.972	High Similarity	NPC97716
0.972	High Similarity	NPC237635
0.972	High Similarity	NPC104406
0.972	High Similarity	NPC79469
0.972	High Similarity	NPC201731
0.972	High Similarity	NPC24673
0.972	High Similarity	NPC473077
0.9718	High Similarity	NPC319752
0.9718	High Similarity	NPC224714
0.966	High Similarity	NPC470681
0.9655	High Similarity	NPC472633
0.9655	High Similarity	NPC61258
0.9653	High Similarity	NPC321623
0.9653	High Similarity	NPC161191
0.9653	High Similarity	NPC244407
0.9653	High Similarity	NPC266572
0.9653	High Similarity	NPC189087
0.965	High Similarity	NPC111786
0.965	High Similarity	NPC301276
0.965	High Similarity	NPC142405
0.965	High Similarity	NPC474161
0.965	High Similarity	NPC476088
0.965	High Similarity	NPC83357
0.965	High Similarity	NPC67805
0.965	High Similarity	NPC54577
0.965	High Similarity	NPC312973
0.965	High Similarity	NPC470647
0.965	High Similarity	NPC20488
0.965	High Similarity	NPC214774
0.965	High Similarity	NPC195621
0.965	High Similarity	NPC267375
0.965	High Similarity	NPC88964
0.965	High Similarity	NPC246948
0.965	High Similarity	NPC475052
0.965	High Similarity	NPC176229
0.965	High Similarity	NPC472629
0.9592	High Similarity	NPC472583
0.9592	High Similarity	NPC223701
0.9592	High Similarity	NPC7989
0.9583	High Similarity	NPC166757
0.9583	High Similarity	NPC283234
0.9583	High Similarity	NPC14001
0.9583	High Similarity	NPC23728
0.9583	High Similarity	NPC110303
0.958	High Similarity	NPC87486
0.958	High Similarity	NPC470890
0.958	High Similarity	NPC124780
0.9577	High Similarity	NPC78803
0.9577	High Similarity	NPC214236
0.9577	High Similarity	NPC217083
0.9577	High Similarity	NPC62840
0.9577	High Similarity	NPC59739
0.9577	High Similarity	NPC299080
0.9577	High Similarity	NPC293852
0.9527	High Similarity	NPC304207
0.9527	High Similarity	NPC48579
0.9527	High Similarity	NPC217706
0.9527	High Similarity	NPC207809
0.9527	High Similarity	NPC259710
0.9524	High Similarity	NPC161881
0.9524	High Similarity	NPC150123
0.9524	High Similarity	NPC475790
0.9524	High Similarity	NPC10807
0.9524	High Similarity	NPC56232
0.9524	High Similarity	NPC244583
0.9521	High Similarity	NPC188403
0.9521	High Similarity	NPC37348
0.9521	High Similarity	NPC471115
0.9521	High Similarity	NPC29777
0.9517	High Similarity	NPC168085
0.9517	High Similarity	NPC160821
0.9517	High Similarity	NPC132592
0.9517	High Similarity	NPC296869
0.9514	High Similarity	NPC220418
0.9514	High Similarity	NPC124729
0.951	High Similarity	NPC214166
0.951	High Similarity	NPC117836
0.951	High Similarity	NPC478086
0.951	High Similarity	NPC51887
0.951	High Similarity	NPC476178
0.951	High Similarity	NPC475705
0.951	High Similarity	NPC219915
0.951	High Similarity	NPC316816
0.9459	High Similarity	NPC469405
0.9459	High Similarity	NPC180301
0.9459	High Similarity	NPC236756
0.9459	High Similarity	NPC311579
0.9459	High Similarity	NPC248793
0.9456	High Similarity	NPC472422
0.9456	High Similarity	NPC209846
0.9456	High Similarity	NPC471676
0.9456	High Similarity	NPC328740
0.9456	High Similarity	NPC472420
0.9456	High Similarity	NPC244577
0.9456	High Similarity	NPC289774
0.9456	High Similarity	NPC471675
0.9456	High Similarity	NPC471677
0.9456	High Similarity	NPC474021
0.9456	High Similarity	NPC474023
0.9456	High Similarity	NPC477897
0.9456	High Similarity	NPC263384
0.9452	High Similarity	NPC470461
0.9452	High Similarity	NPC473016
0.9452	High Similarity	NPC317492
0.9448	High Similarity	NPC222298
0.9448	High Similarity	NPC472627
0.9448	High Similarity	NPC51070
0.9444	High Similarity	NPC273538
0.9444	High Similarity	NPC131568
0.9444	High Similarity	NPC234629
0.9444	High Similarity	NPC311741
0.9444	High Similarity	NPC209040
0.9444	High Similarity	NPC216538
0.9444	High Similarity	NPC131579
0.9441	High Similarity	NPC66515
0.9441	High Similarity	NPC306829
0.9441	High Similarity	NPC296917
0.9441	High Similarity	NPC32739
0.9441	High Similarity	NPC76372
0.9441	High Similarity	NPC226636
0.9441	High Similarity	NPC107572
0.9441	High Similarity	NPC324134
0.9441	High Similarity	NPC166934
0.9441	High Similarity	NPC324436
0.9441	High Similarity	NPC194432
0.9441	High Similarity	NPC11561
0.9441	High Similarity	NPC161506
0.9441	High Similarity	NPC37496
0.9441	High Similarity	NPC177354
0.9441	High Similarity	NPC228504
0.9441	High Similarity	NPC167624
0.9441	High Similarity	NPC227579
0.9441	High Similarity	NPC220998
0.9441	High Similarity	NPC76338
0.9441	High Similarity	NPC78
0.9441	High Similarity	NPC166482
0.9441	High Similarity	NPC223500
0.9441	High Similarity	NPC10937
0.9441	High Similarity	NPC265040
0.9441	High Similarity	NPC64915
0.9441	High Similarity	NPC328164
0.9441	High Similarity	NPC182852
0.9441	High Similarity	NPC40833
0.9441	High Similarity	NPC1089
0.9441	High Similarity	NPC125855
0.9441	High Similarity	NPC148757
0.9437	High Similarity	NPC159275
0.9437	High Similarity	NPC241100
0.9437	High Similarity	NPC150522
0.94	High Similarity	NPC281137
0.94	High Similarity	NPC282390
0.9396	High Similarity	NPC477530
0.9396	High Similarity	NPC304745
0.9396	High Similarity	NPC111341
0.9396	High Similarity	NPC477958
0.9392	High Similarity	NPC285623
0.9392	High Similarity	NPC327269
0.9392	High Similarity	NPC476238
0.9392	High Similarity	NPC31627
0.9388	High Similarity	NPC476185
0.9388	High Similarity	NPC321896
0.9388	High Similarity	NPC474735
0.9384	High Similarity	NPC470460
0.9379	High Similarity	NPC127059
0.9379	High Similarity	NPC470131
0.9379	High Similarity	NPC470134
0.9379	High Similarity	NPC178343
0.9379	High Similarity	NPC24136
0.9379	High Similarity	NPC473078
0.9379	High Similarity	NPC109183
0.9379	High Similarity	NPC470133
0.9379	High Similarity	NPC470132
0.9379	High Similarity	NPC306488
0.9379	High Similarity	NPC187282
0.9379	High Similarity	NPC290133
0.9379	High Similarity	NPC5820
0.9379	High Similarity	NPC470458
0.9379	High Similarity	NPC285630
0.9375	High Similarity	NPC149026
0.9375	High Similarity	NPC212932
0.9375	High Similarity	NPC85162
0.9375	High Similarity	NPC106985
0.9375	High Similarity	NPC150408
0.9375	High Similarity	NPC39329
0.9375	High Similarity	NPC68104
0.9375	High Similarity	NPC9117
0.9375	High Similarity	NPC278249
0.9375	High Similarity	NPC166138
0.9375	High Similarity	NPC107177
0.9375	High Similarity	NPC24821
0.9375	High Similarity	NPC190637
0.9375	High Similarity	NPC81697
0.9375	High Similarity	NPC185276
0.9375	High Similarity	NPC310130
0.9375	High Similarity	NPC18585
0.9375	High Similarity	NPC257097
0.9375	High Similarity	NPC75049
0.9375	High Similarity	NPC38219

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 NPC5173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	918
0.2-0.3	1553
0.3-0.4	2565
0.4-0.5	2007
0.5-0.6	1157
0.6-0.7	405
0.7-0.8	138
0.8-0.85	44
0.85-0.9	20
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9444	High Similarity	NPD4378	Clinical (unspecified phase)
0.9257	High Similarity	NPD4380	Phase 2
0.9178	High Similarity	NPD7410	Clinical (unspecified phase)
0.9091	High Similarity	NPD1552	Clinical (unspecified phase)
0.9091	High Similarity	NPD1550	Clinical (unspecified phase)
0.9073	High Similarity	NPD2393	Clinical (unspecified phase)
0.9028	High Similarity	NPD1549	Phase 2
0.9021	High Similarity	NPD2796	Approved
0.9013	High Similarity	NPD8443	Clinical (unspecified phase)
0.8951	High Similarity	NPD1510	Phase 2
0.8896	High Similarity	NPD4381	Clinical (unspecified phase)
0.8816	High Similarity	NPD7411	Suspended
0.8774	High Similarity	NPD7075	Discontinued
0.8758	High Similarity	NPD6801	Discontinued
0.8758	High Similarity	NPD1934	Approved
0.875	High Similarity	NPD7804	Clinical (unspecified phase)
0.8701	High Similarity	NPD7096	Clinical (unspecified phase)
0.8671	High Similarity	NPD1240	Approved
0.8608	High Similarity	NPD6959	Discontinued
0.86	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD2801	Approved
0.8581	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD6168	Clinical (unspecified phase)
0.8562	High Similarity	NPD6166	Phase 2
0.8562	High Similarity	NPD6167	Clinical (unspecified phase)
0.8552	High Similarity	NPD1607	Approved
0.8487	Intermediate Similarity	NPD1512	Approved
0.8471	Intermediate Similarity	NPD7768	Phase 2
0.8447	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD5403	Approved
0.8405	Intermediate Similarity	NPD7054	Approved
0.84	Intermediate Similarity	NPD3750	Approved
0.8355	Intermediate Similarity	NPD6799	Approved
0.8354	Intermediate Similarity	NPD7472	Approved
0.8354	Intermediate Similarity	NPD7074	Phase 3
0.8344	Intermediate Similarity	NPD3818	Discontinued
0.8333	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5494	Approved
0.8303	Intermediate Similarity	NPD6797	Phase 2
0.8301	Intermediate Similarity	NPD5401	Approved
0.8291	Intermediate Similarity	NPD5402	Approved
0.8291	Intermediate Similarity	NPD3817	Phase 2
0.8253	Intermediate Similarity	NPD7251	Discontinued
0.8239	Intermediate Similarity	NPD3882	Suspended
0.8204	Intermediate Similarity	NPD7808	Phase 3
0.8204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD920	Approved
0.8187	Intermediate Similarity	NPD3749	Approved
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8151	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6559	Discontinued
0.8133	Intermediate Similarity	NPD1551	Phase 2
0.8133	Intermediate Similarity	NPD2935	Discontinued
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD5124	Phase 1
0.8108	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1243	Approved
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8067	Intermediate Similarity	NPD3748	Approved
0.8067	Intermediate Similarity	NPD7033	Discontinued
0.8065	Intermediate Similarity	NPD2532	Approved
0.8065	Intermediate Similarity	NPD2534	Approved
0.8065	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2533	Approved
0.8054	Intermediate Similarity	NPD6651	Approved
0.8052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD4363	Phase 3
0.8046	Intermediate Similarity	NPD4360	Phase 2
0.8039	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2313	Discontinued
0.8027	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7976	Intermediate Similarity	NPD5953	Discontinued
0.7964	Intermediate Similarity	NPD7286	Phase 2
0.7952	Intermediate Similarity	NPD7473	Discontinued
0.7947	Intermediate Similarity	NPD2799	Discontinued
0.7922	Intermediate Similarity	NPD4628	Phase 3
0.7891	Intermediate Similarity	NPD4908	Phase 1
0.7843	Intermediate Similarity	NPD2344	Approved
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6099	Approved
0.7771	Intermediate Similarity	NPD7390	Discontinued
0.7765	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD1548	Phase 1
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1247	Approved
0.7697	Intermediate Similarity	NPD4361	Phase 2
0.7697	Intermediate Similarity	NPD919	Approved
0.7697	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1203	Approved
0.7667	Intermediate Similarity	NPD3268	Approved
0.7663	Intermediate Similarity	NPD7584	Approved
0.7655	Intermediate Similarity	NPD1610	Phase 2
0.7654	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6832	Phase 2
0.7643	Intermediate Similarity	NPD2309	Approved
0.7635	Intermediate Similarity	NPD2798	Approved
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3225	Approved
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.761	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4308	Phase 3
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2797	Approved
0.7566	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1613	Approved
0.7566	Intermediate Similarity	NPD943	Approved
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7531	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6844	Discontinued
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7483	Intermediate Similarity	NPD9717	Approved
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.7456	Intermediate Similarity	NPD5710	Approved
0.7456	Intermediate Similarity	NPD5711	Approved
0.7455	Intermediate Similarity	NPD1465	Phase 2
0.7452	Intermediate Similarity	NPD2424	Discontinued
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD7458	Discontinued
0.7412	Intermediate Similarity	NPD3926	Phase 2
0.741	Intermediate Similarity	NPD4288	Approved
0.7405	Intermediate Similarity	NPD2654	Approved
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD1729	Discontinued
0.7368	Intermediate Similarity	NPD3027	Phase 3
0.7368	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7229	Phase 3
0.7349	Intermediate Similarity	NPD5761	Phase 2
0.7349	Intermediate Similarity	NPD5760	Phase 2
0.7349	Intermediate Similarity	NPD8455	Phase 2
0.7338	Intermediate Similarity	NPD4307	Phase 2
0.7337	Intermediate Similarity	NPD6782	Approved
0.7337	Intermediate Similarity	NPD6781	Approved
0.7337	Intermediate Similarity	NPD6778	Approved
0.7337	Intermediate Similarity	NPD6780	Approved
0.7337	Intermediate Similarity	NPD6777	Approved
0.7337	Intermediate Similarity	NPD6776	Approved
0.7337	Intermediate Similarity	NPD6779	Approved
0.7333	Intermediate Similarity	NPD3267	Approved
0.7333	Intermediate Similarity	NPD5889	Approved
0.7333	Intermediate Similarity	NPD5890	Approved
0.7333	Intermediate Similarity	NPD3266	Approved
0.732	Intermediate Similarity	NPD6798	Discontinued
0.732	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1652	Phase 2
0.729	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD6005	Phase 3
0.7278	Intermediate Similarity	NPD6004	Phase 3
0.7278	Intermediate Similarity	NPD6002	Phase 3
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6585	Discontinued
0.726	Intermediate Similarity	NPD9545	Approved
0.7257	Intermediate Similarity	NPD3823	Discontinued
0.725	Intermediate Similarity	NPD7003	Approved
0.7249	Intermediate Similarity	NPD7585	Approved
0.7248	Intermediate Similarity	NPD1608	Approved
0.7248	Intermediate Similarity	NPD3972	Approved
0.7243	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6273	Approved
0.7237	Intermediate Similarity	NPD2861	Phase 2
0.7237	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7213	Phase 3
0.7222	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD4287	Approved
0.7219	Intermediate Similarity	NPD7696	Phase 3
0.7219	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD7697	Approved
0.7219	Intermediate Similarity	NPD7698	Approved
0.7215	Intermediate Similarity	NPD5408	Approved
0.7215	Intermediate Similarity	NPD5404	Approved
0.7215	Intermediate Similarity	NPD5405	Approved
0.7215	Intermediate Similarity	NPD5406	Approved
0.7208	Intermediate Similarity	NPD1296	Phase 2
0.7208	Intermediate Similarity	NPD3764	Approved
0.7207	Intermediate Similarity	NPD8150	Discontinued
0.72	Intermediate Similarity	NPD4749	Approved
0.7196	Intermediate Similarity	NPD7583	Approved
0.7193	Intermediate Similarity	NPD7199	Phase 2
0.7186	Intermediate Similarity	NPD37	Approved
0.7184	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7871	Phase 2
0.7181	Intermediate Similarity	NPD7870	Phase 2
0.7181	Intermediate Similarity	NPD1201	Approved
0.7179	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD1933	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