NPASS Compound

Structure

CID97812 OpenBabel06191715432D 35 39 0 0 1 0 0 0 0 0999 V2000 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 -1.7321 -1.0000 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 0.8660 -2.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 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 4.3301 -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 1 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 1.7321 -1.0000 0.0000 C 0 0 1 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 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 7 13 2 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 18 29 2 0 0 0 0 19 26 1 0 0 0 0 19 30 1 0 0 0 0 20 27 1 6 0 0 0 20 35 1 0 0 0 0 21 16 1 6 0 0 0 21 34 1 0 0 0 0 22 25 2 0 0 0 0 22 34 1 0 0 0 0 23 31 2 0 0 0 0 23 35 1 0 0 0 0 24 26 1 0 0 0 0 24 27 1 1 0 0 0 25 28 1 0 0 0 0 26 28 2 0 0 0 0 27 32 1 1 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.15
Volume:	479.956
LogP:	4.45
LogD:	2.906
LogS:	-3.92
# Rotatable Bonds:	5
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.126
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.151
MDCK Permeability:	2.124609272868838e-05
Pgp-inhibitor:	0.114
Pgp-substrate:	0.096
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	99.30176544189453%
Volume Distribution (VD):	0.465
Pgp-substrate:	1.184952974319458%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.253
CYP2C9-inhibitor:	0.953
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.806
CYP2D6-substrate:	0.293
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	5.499
Half-life (T1/2):	0.07

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.383
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.164
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.699
Carcinogencity:	0.175
Eye Corrosion:	0.003
Eye Irritation:	0.232
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC97812

Natural Product ID:	NPC97812
*Common Name:**	Goniolactone B
IUPAC Name:	(2S)-5,7-dihydroxy-6-[(1S,2R)-2-hydroxy-2-[(2R)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl]-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	NVXSIKNLZGNCDG-XLQFRCBESA-N
Standard InCHI:	InChI=1S/C28H24O7/c29-18-14-21(16-8-3-1-4-9-16)34-22-15-19(30)26(28(33)25(18)22)24(17-10-5-2-6-11-17)27(32)20-12-7-13-23(31)35-20/h1-11,13,15,20-21,24,27,30,32-33H,12,14H2/t20-,21+,24+,27+/m1/s1
SMILES:	c1ccc(cc1)[C@@H]1CC(=O)c2c(cc(c([C@H](c3ccccc3)[C@H]([C@H]3CC=CC(=O)O3)O)c2O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464289
PubChem CID:	5478949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO21970	Goniothalamus cheliensis	Species	Annonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12088424]
NPO21970	Goniothalamus cheliensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21970	Goniothalamus cheliensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21970	Goniothalamus cheliensis	Species	Annonaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	7400.0	nM	PMID[499310]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	4430.0	nM	PMID[499310]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	7230.0	nM	PMID[499310]

☑ 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 NPC97812 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	381
0.1-0.2	1477
0.2-0.3	3271
0.3-0.4	7832
0.4-0.5	10588
0.5-0.6	4044
0.6-0.7	5213
0.7-0.8	5541
0.8-0.85	2976
0.85-0.9	1270
0.9-0.95	103
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC471787
0.9474	High Similarity	NPC309512
0.9474	High Similarity	NPC148945
0.9474	High Similarity	NPC78835
0.9474	High Similarity	NPC204561
0.9474	High Similarity	NPC317715
0.9474	High Similarity	NPC316960
0.9363	High Similarity	NPC92589
0.9363	High Similarity	NPC175513
0.9355	High Similarity	NPC208152
0.9355	High Similarity	NPC78492
0.9351	High Similarity	NPC109594
0.9351	High Similarity	NPC223701
0.9351	High Similarity	NPC244250
0.9351	High Similarity	NPC326592
0.9351	High Similarity	NPC20907
0.9351	High Similarity	NPC7989
0.9351	High Similarity	NPC112701
0.9351	High Similarity	NPC472583
0.9346	High Similarity	NPC209846
0.9346	High Similarity	NPC477897
0.9346	High Similarity	NPC328740
0.9346	High Similarity	NPC289774
0.9317	High Similarity	NPC76047
0.9286	High Similarity	NPC161881
0.9286	High Similarity	NPC244583
0.9286	High Similarity	NPC56232
0.9286	High Similarity	NPC150123
0.9286	High Similarity	NPC256141
0.9286	High Similarity	NPC10807
0.9281	High Similarity	NPC124478
0.9281	High Similarity	NPC177308
0.9245	High Similarity	NPC63438
0.9241	High Similarity	NPC195685
0.9241	High Similarity	NPC472994
0.9241	High Similarity	NPC210961
0.9241	High Similarity	NPC477629
0.9241	High Similarity	NPC477628
0.9241	High Similarity	NPC270675
0.9236	High Similarity	NPC123544
0.9231	High Similarity	NPC32867
0.9226	High Similarity	NPC469405
0.9226	High Similarity	NPC268193
0.9221	High Similarity	NPC472420
0.9221	High Similarity	NPC472422
0.9221	High Similarity	NPC471676
0.9221	High Similarity	NPC263384
0.9221	High Similarity	NPC244577
0.9182	High Similarity	NPC472876
0.9177	High Similarity	NPC114147
0.9172	High Similarity	NPC318527
0.9172	High Similarity	NPC322459
0.9172	High Similarity	NPC324358
0.9172	High Similarity	NPC323627
0.9172	High Similarity	NPC475184
0.9167	High Similarity	NPC304207
0.9167	High Similarity	NPC304745
0.9167	High Similarity	NPC111341
0.9167	High Similarity	NPC217706
0.9167	High Similarity	NPC207809
0.9167	High Similarity	NPC182555
0.9167	High Similarity	NPC48579
0.9167	High Similarity	NPC477958
0.9167	High Similarity	NPC477530
0.9167	High Similarity	NPC66441
0.9167	High Similarity	NPC470681
0.9167	High Similarity	NPC259710
0.9161	High Similarity	NPC171651
0.9161	High Similarity	NPC243171
0.9161	High Similarity	NPC475790
0.9161	High Similarity	NPC216035
0.9161	High Similarity	NPC35567
0.9161	High Similarity	NPC217149
0.9156	High Similarity	NPC180351
0.9156	High Similarity	NPC474735
0.9141	High Similarity	NPC212038
0.9141	High Similarity	NPC81332
0.9141	High Similarity	NPC271848
0.9141	High Similarity	NPC262580
0.9141	High Similarity	NPC289396
0.913	High Similarity	NPC13481
0.913	High Similarity	NPC207575
0.9125	High Similarity	NPC80068
0.9119	High Similarity	NPC47923
0.9119	High Similarity	NPC114652
0.9114	High Similarity	NPC295090
0.9114	High Similarity	NPC15815
0.9108	High Similarity	NPC469936
0.9108	High Similarity	NPC321372
0.9108	High Similarity	NPC475797
0.9108	High Similarity	NPC474738
0.9108	High Similarity	NPC69531
0.9108	High Similarity	NPC474609
0.9108	High Similarity	NPC129053
0.9108	High Similarity	NPC78554
0.9108	High Similarity	NPC109967
0.9103	High Similarity	NPC293286
0.9103	High Similarity	NPC121568
0.9103	High Similarity	NPC248793
0.9103	High Similarity	NPC180301
0.9097	High Similarity	NPC178484
0.9097	High Similarity	NPC474023
0.9097	High Similarity	NPC209142
0.9097	High Similarity	NPC474021
0.9097	High Similarity	NPC262039
0.9097	High Similarity	NPC471677
0.9097	High Similarity	NPC312549
0.9097	High Similarity	NPC262038
0.9097	High Similarity	NPC254412
0.9097	High Similarity	NPC278476
0.9097	High Similarity	NPC319910
0.9091	High Similarity	NPC164205
0.9091	High Similarity	NPC19238
0.9091	High Similarity	NPC89442
0.9091	High Similarity	NPC139966
0.9091	High Similarity	NPC307052
0.9091	High Similarity	NPC104236
0.9079	High Similarity	NPC470136
0.9079	High Similarity	NPC39045
0.9079	High Similarity	NPC470135
0.9074	High Similarity	NPC260266
0.9068	High Similarity	NPC139060
0.9068	High Similarity	NPC129264
0.9068	High Similarity	NPC85751
0.9068	High Similarity	NPC471788
0.9068	High Similarity	NPC205824
0.9068	High Similarity	NPC19240
0.9062	High Similarity	NPC44947
0.9062	High Similarity	NPC476247
0.9057	High Similarity	NPC271479
0.9057	High Similarity	NPC472320
0.9051	High Similarity	NPC258035
0.9051	High Similarity	NPC257166
0.9051	High Similarity	NPC313163
0.9051	High Similarity	NPC161749
0.9051	High Similarity	NPC197896
0.9051	High Similarity	NPC156457
0.9045	High Similarity	NPC108937
0.9045	High Similarity	NPC476169
0.9045	High Similarity	NPC134171
0.9045	High Similarity	NPC300668
0.9045	High Similarity	NPC279218
0.9038	High Similarity	NPC476238
0.9038	High Similarity	NPC31627
0.9038	High Similarity	NPC473996
0.9038	High Similarity	NPC327269
0.9038	High Similarity	NPC285623
0.9038	High Similarity	NPC138288
0.9038	High Similarity	NPC174086
0.9032	High Similarity	NPC105136
0.9032	High Similarity	NPC29777
0.9032	High Similarity	NPC471115
0.9026	High Similarity	NPC10097
0.9026	High Similarity	NPC122894
0.9026	High Similarity	NPC39195
0.902	High Similarity	NPC470133
0.902	High Similarity	NPC473078
0.902	High Similarity	NPC470134
0.902	High Similarity	NPC470132
0.902	High Similarity	NPC25844
0.902	High Similarity	NPC472629
0.902	High Similarity	NPC109183
0.902	High Similarity	NPC470131
0.9018	High Similarity	NPC53252
0.9012	High Similarity	NPC89809
0.9012	High Similarity	NPC171985
0.9012	High Similarity	NPC473278
0.9012	High Similarity	NPC320741
0.9012	High Similarity	NPC260504
0.9006	High Similarity	NPC257566
0.9006	High Similarity	NPC124155
0.9	High Similarity	NPC303913
0.9	High Similarity	NPC142252
0.8994	High Similarity	NPC117418
0.8994	High Similarity	NPC105584
0.8994	High Similarity	NPC308265
0.8994	High Similarity	NPC73511
0.8994	High Similarity	NPC53545
0.8994	High Similarity	NPC43761
0.8994	High Similarity	NPC51247
0.8987	High Similarity	NPC10754
0.8987	High Similarity	NPC20530
0.8987	High Similarity	NPC309648
0.8987	High Similarity	NPC215917
0.8981	High Similarity	NPC311579
0.8981	High Similarity	NPC236756
0.8981	High Similarity	NPC88983
0.8974	High Similarity	NPC474772
0.8974	High Similarity	NPC472423
0.8974	High Similarity	NPC471675
0.8974	High Similarity	NPC472580
0.8974	High Similarity	NPC474744
0.8974	High Similarity	NPC472636
0.8974	High Similarity	NPC290671
0.8974	High Similarity	NPC295650
0.897	High Similarity	NPC168789
0.8968	High Similarity	NPC164299
0.8968	High Similarity	NPC472628
0.8968	High Similarity	NPC5173
0.8968	High Similarity	NPC3642

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 NPC97812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	875
0.2-0.3	1703
0.3-0.4	2547
0.4-0.5	1913
0.5-0.6	1114
0.6-0.7	429
0.7-0.8	162
0.8-0.85	43
0.85-0.9	23
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD4380	Phase 2
0.9051	High Similarity	NPD7075	Discontinued
0.9051	High Similarity	NPD4381	Clinical (unspecified phase)
0.8981	High Similarity	NPD7096	Clinical (unspecified phase)
0.8974	High Similarity	NPD7411	Suspended
0.8924	High Similarity	NPD8443	Clinical (unspecified phase)
0.8917	High Similarity	NPD6801	Discontinued
0.8834	High Similarity	NPD7852	Clinical (unspecified phase)
0.8788	High Similarity	NPD7804	Clinical (unspecified phase)
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8742	High Similarity	NPD2393	Clinical (unspecified phase)
0.872	High Similarity	NPD6168	Clinical (unspecified phase)
0.872	High Similarity	NPD6167	Clinical (unspecified phase)
0.872	High Similarity	NPD6166	Phase 2
0.871	High Similarity	NPD4378	Clinical (unspecified phase)
0.871	High Similarity	NPD7410	Clinical (unspecified phase)
0.8684	High Similarity	NPD1549	Phase 2
0.8634	High Similarity	NPD7768	Phase 2
0.8625	High Similarity	NPD7819	Suspended
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8599	High Similarity	NPD5403	Approved
0.8563	High Similarity	NPD5844	Phase 1
0.8562	High Similarity	NPD1934	Approved
0.8537	High Similarity	NPD6959	Discontinued
0.8526	High Similarity	NPD6799	Approved
0.8487	Intermediate Similarity	NPD1510	Phase 2
0.8471	Intermediate Similarity	NPD5401	Approved
0.8466	Intermediate Similarity	NPD3749	Approved
0.8462	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD5402	Approved
0.8452	Intermediate Similarity	NPD7054	Approved
0.8452	Intermediate Similarity	NPD3750	Approved
0.8438	Intermediate Similarity	NPD6599	Discontinued
0.8431	Intermediate Similarity	NPD2796	Approved
0.8412	Intermediate Similarity	NPD6559	Discontinued
0.8402	Intermediate Similarity	NPD7074	Phase 3
0.8402	Intermediate Similarity	NPD7472	Approved
0.8393	Intermediate Similarity	NPD3818	Discontinued
0.8387	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD5494	Approved
0.8363	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD6797	Phase 2
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8314	Intermediate Similarity	NPD8312	Approved
0.8314	Intermediate Similarity	NPD8313	Approved
0.8304	Intermediate Similarity	NPD7251	Discontinued
0.8291	Intermediate Similarity	NPD1511	Approved
0.8282	Intermediate Similarity	NPD2801	Approved
0.8263	Intermediate Similarity	NPD6232	Discontinued
0.8256	Intermediate Similarity	NPD7808	Phase 3
0.8217	Intermediate Similarity	NPD4628	Phase 3
0.8187	Intermediate Similarity	NPD1512	Approved
0.8129	Intermediate Similarity	NPD3748	Approved
0.8111	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1240	Approved
0.809	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1551	Phase 2
0.8072	Intermediate Similarity	NPD3882	Suspended
0.8061	Intermediate Similarity	NPD8455	Phase 2
0.8037	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD920	Approved
0.8013	Intermediate Similarity	NPD2799	Discontinued
0.8012	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1607	Approved
0.7974	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2313	Discontinued
0.7962	Intermediate Similarity	NPD2935	Discontinued
0.7952	Intermediate Similarity	NPD1465	Phase 2
0.7927	Intermediate Similarity	NPD7458	Discontinued
0.7925	Intermediate Similarity	NPD1243	Approved
0.7901	Intermediate Similarity	NPD2532	Approved
0.7901	Intermediate Similarity	NPD2534	Approved
0.7901	Intermediate Similarity	NPD2533	Approved
0.7875	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3751	Discontinued
0.7857	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4908	Phase 1
0.7841	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5953	Discontinued
0.7821	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5124	Phase 1
0.7818	Intermediate Similarity	NPD3226	Approved
0.7816	Intermediate Similarity	NPD7286	Phase 2
0.7812	Intermediate Similarity	NPD2800	Approved
0.7802	Intermediate Similarity	NPD4363	Phase 3
0.7802	Intermediate Similarity	NPD4360	Phase 2
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8150	Discontinued
0.7765	Intermediate Similarity	NPD919	Approved
0.7737	Intermediate Similarity	NPD8151	Discontinued
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.7688	Intermediate Similarity	NPD2346	Discontinued
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7673	Intermediate Similarity	NPD7033	Discontinued
0.766	Intermediate Similarity	NPD7435	Discontinued
0.7654	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7003	Approved
0.7647	Intermediate Similarity	NPD1203	Approved
0.7632	Intermediate Similarity	NPD7584	Approved
0.7628	Intermediate Similarity	NPD3268	Approved
0.7628	Intermediate Similarity	NPD6798	Discontinued
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7619	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6781	Approved
0.7594	Intermediate Similarity	NPD6776	Approved
0.7594	Intermediate Similarity	NPD6777	Approved
0.7594	Intermediate Similarity	NPD6779	Approved
0.7594	Intermediate Similarity	NPD6778	Approved
0.7594	Intermediate Similarity	NPD6782	Approved
0.7594	Intermediate Similarity	NPD6780	Approved
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2344	Approved
0.7569	Intermediate Similarity	NPD8434	Phase 2
0.7565	Intermediate Similarity	NPD7783	Phase 2
0.7565	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7228	Approved
0.7547	Intermediate Similarity	NPD6651	Approved
0.7532	Intermediate Similarity	NPD2797	Approved
0.7532	Intermediate Similarity	NPD1613	Approved
0.7532	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7229	Phase 3
0.7516	Intermediate Similarity	NPD5406	Approved
0.7516	Intermediate Similarity	NPD5408	Approved
0.7516	Intermediate Similarity	NPD5404	Approved
0.7516	Intermediate Similarity	NPD5405	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4287	Approved
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4288	Approved
0.7485	Intermediate Similarity	NPD1652	Phase 2
0.7484	Intermediate Similarity	NPD6355	Discontinued
0.7484	Intermediate Similarity	NPD2798	Approved
0.7471	Intermediate Similarity	NPD1247	Approved
0.7471	Intermediate Similarity	NPD37	Approved
0.7469	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6233	Phase 2
0.7457	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4966	Approved
0.7442	Intermediate Similarity	NPD4967	Phase 2
0.7442	Intermediate Similarity	NPD4965	Approved
0.744	Intermediate Similarity	NPD1653	Approved
0.7435	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD7870	Phase 2
0.7429	Intermediate Similarity	NPD5711	Approved
0.7429	Intermediate Similarity	NPD5710	Approved
0.7425	Intermediate Similarity	NPD6273	Approved
0.7423	Intermediate Similarity	NPD7874	Approved
0.7423	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD943	Approved
0.7409	Intermediate Similarity	NPD7585	Approved
0.7407	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD6100	Approved
0.7405	Intermediate Similarity	NPD3764	Approved
0.7394	Intermediate Similarity	NPD2309	Approved
0.7394	Intermediate Similarity	NPD6190	Approved
0.7389	Intermediate Similarity	NPD7685	Pre-registration
0.7386	Intermediate Similarity	NPD3926	Phase 2
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.738	Intermediate Similarity	NPD4361	Phase 2
0.738	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1933	Approved
0.7375	Intermediate Similarity	NPD230	Phase 1
0.7358	Intermediate Similarity	NPD7583	Approved
0.7355	Intermediate Similarity	NPD3225	Approved
0.7346	Intermediate Similarity	NPD4308	Phase 3
0.7345	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD8319	Approved
0.7344	Intermediate Similarity	NPD8320	Phase 1
0.7338	Intermediate Similarity	NPD9717	Approved
0.733	Intermediate Similarity	NPD6823	Phase 2
0.7326	Intermediate Similarity	NPD6534	Approved
0.7326	Intermediate Similarity	NPD6535	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7312	Intermediate Similarity	NPD4060	Phase 1
0.731	Intermediate Similarity	NPD5889	Approved
0.731	Intermediate Similarity	NPD5890	Approved
0.7308	Intermediate Similarity	NPD3266	Approved
0.7308	Intermediate Similarity	NPD3267	Approved
0.7305	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7801	Approved
0.7284	Intermediate Similarity	NPD7097	Phase 1
0.7278	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD447	Suspended
0.7263	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7177	Discontinued
0.7256	Intermediate Similarity	NPD6004	Phase 3
0.7256	Intermediate Similarity	NPD6002	Phase 3

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