NPASS Compound

Structure

NPC474772 OpenBabel07101719522D 32 34 0 0 1 0 0 0 0 0999 V2000 3.9593 -0.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9593 0.5475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 2.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5933 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6713 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8053 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5933 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0933 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6713 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0933 0.0475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 1.7796 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.5374 -0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 1.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5933 -0.8185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7728 2.2796 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 13 2 0 0 0 0 4 14 1 0 0 0 0 5 8 1 0 0 0 0 5 15 2 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 27 2 0 0 0 0 19 20 2 0 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 6 0 0 0 23 25 1 1 0 0 0 23 32 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.18
Volume:	453.09
LogP:	3.093
LogD:	2.115
LogS:	-3.639
# Rotatable Bonds:	7
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	4.196
Fsp3:	0.32
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:	-4.906
MDCK Permeability:	1.5416961105074733e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	100.2430191040039%
Volume Distribution (VD):	0.43
Pgp-substrate:	0.8509536385536194%

ADMET: Metabolism

CYP1A2-inhibitor:	0.257
CYP1A2-substrate:	0.338
CYP2C19-inhibitor:	0.192
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.56
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.646
CYP2D6-substrate:	0.424
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	8.282
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.164
AMES Toxicity:	0.188
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.428
Skin Sensitization:	0.529
Carcinogencity:	0.854
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.678

Download Data

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

Natural Product: NPC474772

Natural Product ID:	NPC474772
*Common Name:**	Xanthokeismins B
IUPAC Name:	(E)-1-[(2S,3S)-2-[(E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-3,4-dihydroxy-2,3-dihydro-1-benzofuran-5-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:	xanthokeismins B
Standard InCHIKey:	SWONFSQDRVSFHS-VIUSQTLFSA-N
Standard InCHI:	InChI=1S/C25H28O7/c1-24(2,30)13-4-14-25(3,31)23-22(29)20-19(32-23)12-10-17(21(20)28)18(27)11-7-15-5-8-16(26)9-6-15/h4-13,22-23,26,28-31H,14H2,1-3H3/b11-7+,13-4+/t22-,23-,25?/m0/s1
SMILES:	Oc1ccc(cc1)/C=C/C(=O)c1ccc2c(c1O)[C@H](O)[C@H](O2)C(C/C=C/C(O)(C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482098
PubChem CID:	24970765
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003542] Furanochalcones

*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
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21056	Angelica keiskei	Species	Apiaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	690.0	nM	PMID[449619]

☑ 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 NPC474772 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	371
0.1-0.2	1372
0.2-0.3	3382
0.3-0.4	8320
0.4-0.5	10160
0.5-0.6	3729
0.6-0.7	5073
0.7-0.8	5658
0.8-0.85	2635
0.85-0.9	1399
0.9-0.95	542
0.95-1	56

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472423
1.0	High Similarity	NPC474744
0.9931	High Similarity	NPC472421
0.9795	High Similarity	NPC476238
0.9795	High Similarity	NPC327269
0.9795	High Similarity	NPC285623
0.9795	High Similarity	NPC473996
0.9795	High Similarity	NPC31627
0.9726	High Similarity	NPC263384
0.9726	High Similarity	NPC472420
0.9726	High Similarity	NPC472422
0.9726	High Similarity	NPC472636
0.9726	High Similarity	NPC471676
0.9726	High Similarity	NPC472580
0.9726	High Similarity	NPC471675
0.9726	High Similarity	NPC244577
0.9722	High Similarity	NPC14875
0.966	High Similarity	NPC477957
0.9653	High Similarity	NPC316769
0.9595	High Similarity	NPC472583
0.9595	High Similarity	NPC223701
0.9595	High Similarity	NPC7989
0.9592	High Similarity	NPC471677
0.9586	High Similarity	NPC202494
0.953	High Similarity	NPC470681
0.953	High Similarity	NPC477958
0.9527	High Similarity	NPC35567
0.9527	High Similarity	NPC475790
0.9527	High Similarity	NPC243171
0.9527	High Similarity	NPC171651
0.9521	High Similarity	NPC168085
0.9463	High Similarity	NPC293286
0.9463	High Similarity	NPC469405
0.9459	High Similarity	NPC474023
0.9459	High Similarity	NPC254412
0.9459	High Similarity	NPC262038
0.9459	High Similarity	NPC262039
0.9459	High Similarity	NPC278476
0.9459	High Similarity	NPC319910
0.9459	High Similarity	NPC474021
0.9456	High Similarity	NPC89442
0.9456	High Similarity	NPC472628
0.9456	High Similarity	NPC317492
0.9452	High Similarity	NPC470670
0.9452	High Similarity	NPC47388
0.9452	High Similarity	NPC473133
0.9452	High Similarity	NPC222298
0.9452	High Similarity	NPC472627
0.9452	High Similarity	NPC51070
0.9452	High Similarity	NPC91902
0.9448	High Similarity	NPC297788
0.9408	High Similarity	NPC328102
0.94	High Similarity	NPC279218
0.94	High Similarity	NPC304207
0.94	High Similarity	NPC48579
0.94	High Similarity	NPC207809
0.94	High Similarity	NPC108937
0.94	High Similarity	NPC217706
0.94	High Similarity	NPC259710
0.9396	High Similarity	NPC138288
0.9396	High Similarity	NPC56232
0.9396	High Similarity	NPC161881
0.9396	High Similarity	NPC10807
0.9396	High Similarity	NPC150123
0.9396	High Similarity	NPC244583
0.9396	High Similarity	NPC216035
0.9396	High Similarity	NPC217149
0.9392	High Similarity	NPC105136
0.9392	High Similarity	NPC61258
0.9384	High Similarity	NPC472629
0.9375	High Similarity	NPC171870
0.9375	High Similarity	NPC470087
0.9375	High Similarity	NPC321980
0.9375	High Similarity	NPC74397
0.9351	High Similarity	NPC124038
0.9351	High Similarity	NPC471286
0.9346	High Similarity	NPC45124
0.9346	High Similarity	NPC30655
0.9346	High Similarity	NPC74854
0.9346	High Similarity	NPC92589
0.9338	High Similarity	NPC10754
0.9338	High Similarity	NPC321372
0.9338	High Similarity	NPC474609
0.9338	High Similarity	NPC78554
0.9338	High Similarity	NPC109967
0.9338	High Similarity	NPC208152
0.9338	High Similarity	NPC129053
0.9338	High Similarity	NPC20530
0.9338	High Similarity	NPC474738
0.9338	High Similarity	NPC469936
0.9338	High Similarity	NPC215917
0.9338	High Similarity	NPC78492
0.9338	High Similarity	NPC475797
0.9333	High Similarity	NPC248793
0.9333	High Similarity	NPC180301
0.9329	High Similarity	NPC289774
0.9329	High Similarity	NPC477897
0.9329	High Similarity	NPC328740
0.9329	High Similarity	NPC209846
0.9324	High Similarity	NPC296030
0.9324	High Similarity	NPC39929
0.9324	High Similarity	NPC5173
0.932	High Similarity	NPC85773
0.9315	High Similarity	NPC224714
0.9315	High Similarity	NPC87486
0.9315	High Similarity	NPC209040
0.9315	High Similarity	NPC124780
0.9315	High Similarity	NPC470857
0.9315	High Similarity	NPC470890
0.931	High Similarity	NPC130206
0.9286	High Similarity	NPC472635
0.9281	High Similarity	NPC220582
0.9281	High Similarity	NPC471976
0.9281	High Similarity	NPC304839
0.9281	High Similarity	NPC472624
0.9281	High Similarity	NPC306978
0.9272	High Similarity	NPC477530
0.9272	High Similarity	NPC111341
0.9272	High Similarity	NPC304745
0.9267	High Similarity	NPC256141
0.9267	High Similarity	NPC210597
0.9262	High Similarity	NPC476509
0.9262	High Similarity	NPC124478
0.9262	High Similarity	NPC177308
0.9262	High Similarity	NPC321896
0.9262	High Similarity	NPC476185
0.9257	High Similarity	NPC6511
0.9257	High Similarity	NPC10097
0.9252	High Similarity	NPC474302
0.9247	High Similarity	NPC478086
0.9247	High Similarity	NPC75049
0.9247	High Similarity	NPC117836
0.9247	High Similarity	NPC310130
0.9247	High Similarity	NPC257097
0.9247	High Similarity	NPC164980
0.9247	High Similarity	NPC149026
0.9247	High Similarity	NPC301751
0.9247	High Similarity	NPC214166
0.9247	High Similarity	NPC169591
0.9247	High Similarity	NPC39329
0.9247	High Similarity	NPC18886
0.9247	High Similarity	NPC175504
0.9247	High Similarity	NPC18585
0.9247	High Similarity	NPC143896
0.9247	High Similarity	NPC51887
0.9247	High Similarity	NPC166138
0.9247	High Similarity	NPC221432
0.9247	High Similarity	NPC150408
0.9247	High Similarity	NPC316816
0.9247	High Similarity	NPC245482
0.9247	High Similarity	NPC91560
0.9247	High Similarity	NPC106985
0.9247	High Similarity	NPC476178
0.9247	High Similarity	NPC475705
0.9247	High Similarity	NPC68104
0.9241	High Similarity	NPC470089
0.9236	High Similarity	NPC470211
0.9236	High Similarity	NPC37206
0.9236	High Similarity	NPC137009
0.9231	High Similarity	NPC119589
0.9226	High Similarity	NPC472581
0.9226	High Similarity	NPC472582
0.9221	High Similarity	NPC3629
0.9205	High Similarity	NPC100134
0.9205	High Similarity	NPC236756
0.9205	High Similarity	NPC326592
0.9205	High Similarity	NPC311579
0.9205	High Similarity	NPC20907
0.9205	High Similarity	NPC268193
0.9205	High Similarity	NPC209760
0.9205	High Similarity	NPC112701
0.9205	High Similarity	NPC109594
0.9205	High Similarity	NPC244250
0.92	High Similarity	NPC318424
0.92	High Similarity	NPC471229
0.9195	High Similarity	NPC226644
0.9195	High Similarity	NPC139966
0.9195	High Similarity	NPC307052
0.9195	High Similarity	NPC37226
0.9189	High Similarity	NPC24673
0.9189	High Similarity	NPC122828
0.9189	High Similarity	NPC40086
0.9189	High Similarity	NPC472918
0.9189	High Similarity	NPC237635
0.9189	High Similarity	NPC104406
0.9189	High Similarity	NPC201731
0.9189	High Similarity	NPC79469
0.9189	High Similarity	NPC110303
0.9189	High Similarity	NPC3779
0.9189	High Similarity	NPC176869
0.9189	High Similarity	NPC476182
0.9189	High Similarity	NPC44721
0.9189	High Similarity	NPC12148
0.9189	High Similarity	NPC130581
0.9189	High Similarity	NPC473077
0.9189	High Similarity	NPC97716
0.9189	High Similarity	NPC23728
0.9189	High Similarity	NPC296998
0.9189	High Similarity	NPC211466
0.9184	High Similarity	NPC311741

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 NPC474772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	850
0.2-0.3	1651
0.3-0.4	2533
0.4-0.5	1955
0.5-0.6	1110
0.6-0.7	491
0.7-0.8	174
0.8-0.85	37
0.85-0.9	20
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9262	High Similarity	NPD4380	Phase 2
0.9079	High Similarity	NPD2393	Clinical (unspecified phase)
0.9054	High Similarity	NPD4378	Clinical (unspecified phase)
0.9026	High Similarity	NPD7075	Discontinued
0.8954	High Similarity	NPD7096	Clinical (unspecified phase)
0.8904	High Similarity	NPD1549	Phase 2
0.8903	High Similarity	NPD4381	Clinical (unspecified phase)
0.8889	High Similarity	NPD1934	Approved
0.8889	High Similarity	NPD6801	Discontinued
0.8839	High Similarity	NPD3882	Suspended
0.8836	High Similarity	NPD1550	Clinical (unspecified phase)
0.8836	High Similarity	NPD1552	Clinical (unspecified phase)
0.88	High Similarity	NPD7410	Clinical (unspecified phase)
0.8767	High Similarity	NPD2796	Approved
0.8733	High Similarity	NPD6799	Approved
0.8699	High Similarity	NPD1510	Phase 2
0.8696	High Similarity	NPD3818	Discontinued
0.8681	High Similarity	NPD1240	Approved
0.8654	High Similarity	NPD8443	Clinical (unspecified phase)
0.8642	High Similarity	NPD7804	Clinical (unspecified phase)
0.8598	High Similarity	NPD6559	Discontinued
0.859	High Similarity	NPD2801	Approved
0.8581	High Similarity	NPD7411	Suspended
0.8571	High Similarity	NPD6166	Phase 2
0.8571	High Similarity	NPD6168	Clinical (unspecified phase)
0.8571	High Similarity	NPD6167	Clinical (unspecified phase)
0.8562	High Similarity	NPD1607	Approved
0.8553	High Similarity	NPD5494	Approved
0.8516	High Similarity	NPD6599	Discontinued
0.8487	Intermediate Similarity	NPD1511	Approved
0.8471	Intermediate Similarity	NPD7819	Suspended
0.8467	Intermediate Similarity	NPD2800	Approved
0.8377	Intermediate Similarity	NPD1512	Approved
0.8364	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD920	Approved
0.8323	Intermediate Similarity	NPD5403	Approved
0.8303	Intermediate Similarity	NPD7054	Approved
0.8302	Intermediate Similarity	NPD3817	Phase 2
0.8289	Intermediate Similarity	NPD4628	Phase 3
0.8272	Intermediate Similarity	NPD6959	Discontinued
0.8253	Intermediate Similarity	NPD7472	Approved
0.825	Intermediate Similarity	NPD7768	Phase 2
0.825	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1243	Approved
0.8204	Intermediate Similarity	NPD6797	Phase 2
0.8199	Intermediate Similarity	NPD3749	Approved
0.8194	Intermediate Similarity	NPD2532	Approved
0.8194	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2533	Approved
0.8194	Intermediate Similarity	NPD2534	Approved
0.8194	Intermediate Similarity	NPD5401	Approved
0.8187	Intermediate Similarity	NPD5402	Approved
0.8182	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7251	Discontinued
0.8146	Intermediate Similarity	NPD1551	Phase 2
0.8146	Intermediate Similarity	NPD2935	Discontinued
0.8107	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7808	Phase 3
0.8092	Intermediate Similarity	NPD2344	Approved
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8052	Intermediate Similarity	NPD3750	Approved
0.8049	Intermediate Similarity	NPD1247	Approved
0.8041	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5953	Discontinued
0.7976	Intermediate Similarity	NPD7286	Phase 2
0.7964	Intermediate Similarity	NPD7473	Discontinued
0.7961	Intermediate Similarity	NPD2799	Discontinued
0.7947	Intermediate Similarity	NPD6651	Approved
0.7935	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2309	Approved
0.7882	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD3926	Phase 2
0.7843	Intermediate Similarity	NPD7033	Discontinued
0.7815	Intermediate Similarity	NPD943	Approved
0.7806	Intermediate Similarity	NPD2424	Discontinued
0.78	Intermediate Similarity	NPD2313	Discontinued
0.7765	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3748	Approved
0.7714	Intermediate Similarity	NPD8434	Phase 2
0.7703	Intermediate Similarity	NPD1203	Approved
0.7697	Intermediate Similarity	NPD1613	Approved
0.7697	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7584	Approved
0.7671	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6832	Phase 2
0.7654	Intermediate Similarity	NPD4360	Phase 2
0.7654	Intermediate Similarity	NPD3226	Approved
0.7654	Intermediate Similarity	NPD4363	Phase 3
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1729	Discontinued
0.7616	Intermediate Similarity	NPD3027	Phase 3
0.7613	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4361	Phase 2
0.7611	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3751	Discontinued
0.7576	Intermediate Similarity	NPD1465	Phase 2
0.7574	Intermediate Similarity	NPD5710	Approved
0.7574	Intermediate Similarity	NPD5711	Approved
0.7564	Intermediate Similarity	NPD6099	Approved
0.7564	Intermediate Similarity	NPD6100	Approved
0.755	Intermediate Similarity	NPD4908	Phase 1
0.7543	Intermediate Similarity	NPD8313	Approved
0.7543	Intermediate Similarity	NPD8312	Approved
0.7532	Intermediate Similarity	NPD5124	Phase 1
0.7532	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6355	Discontinued
0.7516	Intermediate Similarity	NPD4662	Approved
0.7516	Intermediate Similarity	NPD4661	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7516	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD9717	Approved
0.7485	Intermediate Similarity	NPD2403	Approved
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7471	Intermediate Similarity	NPD3823	Discontinued
0.747	Intermediate Similarity	NPD5761	Phase 2
0.747	Intermediate Similarity	NPD5760	Phase 2
0.7455	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7390	Discontinued
0.7451	Intermediate Similarity	NPD6798	Discontinued
0.7446	Intermediate Similarity	NPD6780	Approved
0.7446	Intermediate Similarity	NPD6777	Approved
0.7446	Intermediate Similarity	NPD6778	Approved
0.7446	Intermediate Similarity	NPD6782	Approved
0.7446	Intermediate Similarity	NPD6781	Approved
0.7446	Intermediate Similarity	NPD6776	Approved
0.7446	Intermediate Similarity	NPD6779	Approved
0.7439	Intermediate Similarity	NPD7458	Discontinued
0.7434	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1610	Phase 2
0.7419	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD447	Suspended
0.7417	Intermediate Similarity	NPD2798	Approved
0.741	Intermediate Similarity	NPD37	Approved
0.7407	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6002	Phase 3
0.7405	Intermediate Similarity	NPD6005	Phase 3
0.7405	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6004	Phase 3
0.7405	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD4308	Phase 3
0.7384	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7229	Phase 3
0.7365	Intermediate Similarity	NPD8455	Phase 2
0.7362	Intermediate Similarity	NPD5049	Phase 3
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2354	Approved
0.7329	Intermediate Similarity	NPD6190	Approved
0.7329	Intermediate Similarity	NPD3887	Approved
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7435	Discontinued
0.7321	Intermediate Similarity	NPD2296	Approved
0.7318	Intermediate Similarity	NPD8150	Discontinued
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7312	Intermediate Similarity	NPD1652	Phase 2
0.7308	Intermediate Similarity	NPD1933	Approved
0.7296	Intermediate Similarity	NPD1471	Phase 3
0.729	Intermediate Similarity	NPD6233	Phase 2
0.7279	Intermediate Similarity	NPD9545	Approved
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7267	Intermediate Similarity	NPD3972	Approved
0.7263	Intermediate Similarity	NPD7585	Approved
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.7238	Intermediate Similarity	NPD4287	Approved
0.7237	Intermediate Similarity	NPD2797	Approved
0.7234	Intermediate Similarity	NPD7697	Approved
0.7234	Intermediate Similarity	NPD7698	Approved
0.7234	Intermediate Similarity	NPD7696	Phase 3
0.7225	Intermediate Similarity	NPD8151	Discontinued
0.7211	Intermediate Similarity	NPD7583	Approved
0.7202	Intermediate Similarity	NPD6280	Approved
0.7202	Intermediate Similarity	NPD6844	Discontinued
0.7202	Intermediate Similarity	NPD6279	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.7196	Intermediate Similarity	NPD7871	Phase 2

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