NPASS Compound

Structure

NPC179947 OpenBabel07101719252D 49 55 0 0 1 0 0 0 0 0999 V2000 -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 -9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 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 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 2 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 -8.6603 -2.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 -11.2583 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 10 1 0 0 0 0 2 14 1 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 8 1 0 0 0 0 4 15 2 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 33 1 0 0 0 0 8 34 1 0 0 0 0 9 18 1 0 0 0 0 9 23 1 0 0 0 0 10 30 2 0 0 0 0 10 35 1 0 0 0 0 11 19 2 0 0 0 0 11 36 1 0 0 0 0 12 18 1 0 0 0 0 12 37 1 0 0 0 0 13 31 2 0 0 0 0 13 38 1 0 0 0 0 14 21 2 0 0 0 0 14 48 1 0 0 0 0 15 19 1 0 0 0 0 15 46 1 0 0 0 0 16 20 2 0 0 0 0 16 47 1 0 0 0 0 17 7 1 6 0 0 0 17 24 1 0 0 0 0 17 49 1 0 0 0 0 18 25 2 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 20 27 1 0 0 0 0 21 27 1 0 0 0 0 21 30 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 22 31 1 0 0 0 0 23 39 1 0 0 0 0 24 28 1 0 0 0 0 24 40 1 1 0 0 0 25 41 1 0 0 0 0 26 42 2 0 0 0 0 27 43 2 0 0 0 0 28 29 1 0 0 0 0 28 44 1 6 0 0 0 29 32 1 0 0 0 0 29 45 1 1 0 0 0 30 47 1 0 0 0 0 31 46 1 0 0 0 0 32 48 1 6 0 0 0 32 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	680.1
Volume:	614.656
LogP:	1.868
LogD:	1.093
LogS:	-5.362
# Rotatable Bonds:	4
TPSA:	301.41
# H-Bond Aceptor:	17
# H-Bond Donor:	11
# Rings:	7
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.091
Synthetic Accessibility Score:	4.807
Fsp3:	0.188
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.494
MDCK Permeability:	4.696093128586654e-06
Pgp-inhibitor:	0.034
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.954
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	83.66842651367188%
Volume Distribution (VD):	0.579
Pgp-substrate:	35.56798553466797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.466
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.449
CYP2C9-substrate:	0.159
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	1.865
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.503
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.71
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.828
Respiratory Toxicity:	0.007

Download Data

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

Natural Product: NPC179947

Natural Product ID:	NPC179947
*Common Name:**	Swertiabisxanthone I
IUPAC Name:	1,3,5-trihydroxy-2-(1,4,6,8-tetrahydroxy-9-oxoxanthen-2-yl)-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
Synonyms:	swertiabisxanthone I
Standard InCHIKey:	ABLXWIMCGCHYDR-URIXXQQVSA-N
Standard InCHI:	InChI=1S/C32H24O17/c33-7-17-24(40)28(44)29(45)32(49-17)48-14-2-1-10(35)30-21(14)27(43)20-16(47-30)6-12(37)18(25(20)41)9-5-13(38)31-22(23(9)39)26(42)19-11(36)3-8(34)4-15(19)46-31/h1-6,17,24,28-29,32-41,44-45H,7H2/t17-,24-,28+,29-,32-/m1/s1
SMILES:	c1cc(c2c(=O)c3c(cc(c(c4cc(c5c(c4O)c(=O)c4c(cc(cc4o5)O)O)O)c3O)O)oc2c1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1214706
PubChem CID:	24878847
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/jo00025a032]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50072a022]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20677781]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14238	Swertia punicea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14238	Swertia punicea	Species	Gentianaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	123.0	%	PMID[448232]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	89.1	%	PMID[448232]

☑ 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 NPC179947 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	519
0.1-0.2	2027
0.2-0.3	4540
0.3-0.4	10065
0.4-0.5	7830
0.5-0.6	4501
0.6-0.7	5522
0.7-0.8	4834
0.8-0.85	1627
0.85-0.9	808
0.9-0.95	414
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9942	High Similarity	NPC473618
0.9651	High Similarity	NPC49690
0.9593	High Similarity	NPC132111
0.9538	High Similarity	NPC318119
0.9532	High Similarity	NPC265380
0.948	High Similarity	NPC321916
0.9477	High Similarity	NPC324742
0.9477	High Similarity	NPC185275
0.9382	High Similarity	NPC477082
0.9379	High Similarity	NPC264302
0.9375	High Similarity	NPC477083
0.9375	High Similarity	NPC477081
0.9371	High Similarity	NPC261623
0.9371	High Similarity	NPC111490
0.9368	High Similarity	NPC476203
0.9357	High Similarity	NPC51774
0.9357	High Similarity	NPC239549
0.9357	High Similarity	NPC236191
0.9322	High Similarity	NPC160543
0.9322	High Similarity	NPC187632
0.9322	High Similarity	NPC472721
0.9322	High Similarity	NPC469652
0.9322	High Similarity	NPC472724
0.9322	High Similarity	NPC93065
0.9322	High Similarity	NPC472720
0.9322	High Similarity	NPC31208
0.9314	High Similarity	NPC231254
0.9306	High Similarity	NPC476618
0.9306	High Similarity	NPC476622
0.9306	High Similarity	NPC471789
0.9306	High Similarity	NPC476620
0.9306	High Similarity	NPC476623
0.9306	High Similarity	NPC476619
0.9306	High Similarity	NPC476621
0.9302	High Similarity	NPC142996
0.9302	High Similarity	NPC102028
0.9298	High Similarity	NPC267254
0.9298	High Similarity	NPC301683
0.9298	High Similarity	NPC259152
0.9298	High Similarity	NPC3583
0.9298	High Similarity	NPC156977
0.9294	High Similarity	NPC471457
0.9294	High Similarity	NPC170675
0.9294	High Similarity	NPC112755
0.9266	High Similarity	NPC158214
0.9266	High Similarity	NPC223534
0.9266	High Similarity	NPC290289
0.9266	High Similarity	NPC240200
0.9261	High Similarity	NPC469650
0.9249	High Similarity	NPC255799
0.9244	High Similarity	NPC168789
0.924	High Similarity	NPC34287
0.924	High Similarity	NPC218488
0.924	High Similarity	NPC22195
0.924	High Similarity	NPC21190
0.924	High Similarity	NPC471416
0.924	High Similarity	NPC183357
0.9209	High Similarity	NPC469649
0.9209	High Similarity	NPC64755
0.9209	High Similarity	NPC260521
0.9209	High Similarity	NPC65489
0.9205	High Similarity	NPC148710
0.9195	High Similarity	NPC472387
0.9191	High Similarity	NPC472607
0.9186	High Similarity	NPC180918
0.9186	High Similarity	NPC256760
0.9181	High Similarity	NPC95855
0.9181	High Similarity	NPC472381
0.9181	High Similarity	NPC472383
0.9181	High Similarity	NPC105283
0.9181	High Similarity	NPC210042
0.9176	High Similarity	NPC272560
0.9162	High Similarity	NPC40078
0.9162	High Similarity	NPC471091
0.9162	High Similarity	NPC97924
0.9148	High Similarity	NPC129533
0.9148	High Similarity	NPC123259
0.9138	High Similarity	NPC472991
0.9138	High Similarity	NPC472992
0.9138	High Similarity	NPC8573
0.9138	High Similarity	NPC169733
0.9133	High Similarity	NPC204693
0.9133	High Similarity	NPC208668
0.9133	High Similarity	NPC25724
0.9128	High Similarity	NPC194483
0.9128	High Similarity	NPC150767
0.9128	High Similarity	NPC44328
0.9128	High Similarity	NPC78734
0.9128	High Similarity	NPC105095
0.9128	High Similarity	NPC474434
0.9128	High Similarity	NPC79056
0.9128	High Similarity	NPC293004
0.9128	High Similarity	NPC44558
0.9128	High Similarity	NPC177731
0.9128	High Similarity	NPC52353
0.9123	High Similarity	NPC93099
0.9123	High Similarity	NPC146792
0.9123	High Similarity	NPC45400
0.9123	High Similarity	NPC477502
0.9123	High Similarity	NPC45618
0.9123	High Similarity	NPC58716
0.9091	High Similarity	NPC8940
0.9086	High Similarity	NPC475261
0.9086	High Similarity	NPC168584
0.9086	High Similarity	NPC267549
0.908	High Similarity	NPC198199
0.908	High Similarity	NPC108202
0.9075	High Similarity	NPC205076
0.9075	High Similarity	NPC67134
0.9075	High Similarity	NPC472454
0.9075	High Similarity	NPC307518
0.9075	High Similarity	NPC212038
0.9075	High Similarity	NPC81332
0.9075	High Similarity	NPC262580
0.9075	High Similarity	NPC257667
0.9075	High Similarity	NPC289396
0.9075	High Similarity	NPC48773
0.9075	High Similarity	NPC186847
0.9075	High Similarity	NPC472386
0.9075	High Similarity	NPC47140
0.9075	High Similarity	NPC271848
0.9071	High Similarity	NPC174140
0.907	High Similarity	NPC201292
0.907	High Similarity	NPC226294
0.907	High Similarity	NPC186807
0.907	High Similarity	NPC475212
0.907	High Similarity	NPC43587
0.907	High Similarity	NPC93337
0.907	High Similarity	NPC86008
0.907	High Similarity	NPC45638
0.907	High Similarity	NPC105025
0.907	High Similarity	NPC183036
0.907	High Similarity	NPC469931
0.907	High Similarity	NPC293629
0.907	High Similarity	NPC58053
0.907	High Similarity	NPC475942
0.907	High Similarity	NPC229687
0.9066	High Similarity	NPC3474
0.9064	High Similarity	NPC224851
0.9064	High Similarity	NPC5778
0.9064	High Similarity	NPC8856
0.9064	High Similarity	NPC236934
0.9059	High Similarity	NPC29830
0.905	High Similarity	NPC269046
0.9045	High Similarity	NPC87583
0.904	High Similarity	NPC473883
0.904	High Similarity	NPC97119
0.904	High Similarity	NPC297503
0.904	High Similarity	NPC135831
0.9034	High Similarity	NPC473895
0.9034	High Similarity	NPC473682
0.9034	High Similarity	NPC470443
0.9034	High Similarity	NPC126784
0.9034	High Similarity	NPC110941
0.9034	High Similarity	NPC80956
0.9034	High Similarity	NPC473571
0.9034	High Similarity	NPC470444
0.9034	High Similarity	NPC241423
0.9034	High Similarity	NPC471030
0.9029	High Similarity	NPC65563
0.9029	High Similarity	NPC219043
0.9029	High Similarity	NPC268533
0.9029	High Similarity	NPC67629
0.9029	High Similarity	NPC79736
0.9029	High Similarity	NPC470949
0.9023	High Similarity	NPC172033
0.9023	High Similarity	NPC88560
0.9023	High Similarity	NPC175230
0.9022	High Similarity	NPC470450
0.9017	High Similarity	NPC149011
0.9017	High Similarity	NPC245014
0.9017	High Similarity	NPC231194
0.9017	High Similarity	NPC224462
0.9017	High Similarity	NPC51326
0.9017	High Similarity	NPC204937
0.9017	High Similarity	NPC282987
0.9017	High Similarity	NPC105511
0.9017	High Similarity	NPC285197
0.9017	High Similarity	NPC84265
0.9012	High Similarity	NPC14662
0.9006	High Similarity	NPC165720
0.9006	High Similarity	NPC477840
0.9	High Similarity	NPC201814
0.9	High Similarity	NPC477841
0.8994	High Similarity	NPC97817
0.8994	High Similarity	NPC72554
0.8994	High Similarity	NPC237202
0.8994	High Similarity	NPC30011
0.8994	High Similarity	NPC105591
0.8989	High Similarity	NPC470451
0.8989	High Similarity	NPC470416
0.8989	High Similarity	NPC470455
0.8983	High Similarity	NPC473073
0.8983	High Similarity	NPC473071
0.8983	High Similarity	NPC469371
0.8977	High Similarity	NPC120952
0.8977	High Similarity	NPC251417
0.8977	High Similarity	NPC89052
0.8971	High Similarity	NPC294629
0.8966	High Similarity	NPC60735

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 NPC179947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	447
0.1-0.2	1004
0.2-0.3	2100
0.3-0.4	2707
0.4-0.5	1710
0.5-0.6	806
0.6-0.7	234
0.7-0.8	105
0.8-0.85	22
0.85-0.9	9
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9128	High Similarity	NPD7074	Phase 3
0.9017	High Similarity	NPD7472	Approved
0.896	High Similarity	NPD7054	Approved
0.8864	High Similarity	NPD4338	Clinical (unspecified phase)
0.8864	High Similarity	NPD7808	Phase 3
0.8857	High Similarity	NPD6797	Phase 2
0.8807	High Similarity	NPD7251	Discontinued
0.8793	High Similarity	NPD3818	Discontinued
0.8786	High Similarity	NPD6168	Clinical (unspecified phase)
0.8786	High Similarity	NPD6167	Clinical (unspecified phase)
0.8786	High Similarity	NPD6166	Phase 2
0.8644	High Similarity	NPD7993	Clinical (unspecified phase)
0.8636	High Similarity	NPD7804	Clinical (unspecified phase)
0.8547	High Similarity	NPD4381	Clinical (unspecified phase)
0.85	High Similarity	NPD8313	Approved
0.85	High Similarity	NPD8312	Approved
0.848	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.847	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1934	Approved
0.84	Intermediate Similarity	NPD6959	Discontinued
0.8382	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD2801	Approved
0.8343	Intermediate Similarity	NPD5494	Approved
0.8324	Intermediate Similarity	NPD5844	Phase 1
0.8287	Intermediate Similarity	NPD6559	Discontinued
0.828	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD8455	Phase 2
0.8198	Intermediate Similarity	NPD4380	Phase 2
0.8156	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD6232	Discontinued
0.8114	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD8151	Discontinued
0.8111	Intermediate Similarity	NPD7473	Discontinued
0.803	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD7783	Phase 2
0.7967	Intermediate Similarity	NPD7228	Approved
0.7966	Intermediate Similarity	NPD3882	Suspended
0.7955	Intermediate Similarity	NPD1465	Phase 2
0.7953	Intermediate Similarity	NPD1511	Approved
0.7944	Intermediate Similarity	NPD3787	Discontinued
0.7921	Intermediate Similarity	NPD7075	Discontinued
0.791	Intermediate Similarity	NPD3817	Phase 2
0.7887	Intermediate Similarity	NPD6780	Approved
0.7887	Intermediate Similarity	NPD6781	Approved
0.7887	Intermediate Similarity	NPD6778	Approved
0.7887	Intermediate Similarity	NPD6777	Approved
0.7887	Intermediate Similarity	NPD6779	Approved
0.7887	Intermediate Similarity	NPD6782	Approved
0.7887	Intermediate Similarity	NPD6776	Approved
0.7869	Intermediate Similarity	NPD3751	Discontinued
0.7865	Intermediate Similarity	NPD7768	Phase 2
0.7861	Intermediate Similarity	NPD1512	Approved
0.7857	Intermediate Similarity	NPD7697	Approved
0.7857	Intermediate Similarity	NPD7698	Approved
0.7857	Intermediate Similarity	NPD7696	Phase 3
0.7853	Intermediate Similarity	NPD7819	Suspended
0.7841	Intermediate Similarity	NPD7411	Suspended
0.7817	Intermediate Similarity	NPD7871	Phase 2
0.7817	Intermediate Similarity	NPD7870	Phase 2
0.7809	Intermediate Similarity	NPD5402	Approved
0.7789	Intermediate Similarity	NPD7701	Phase 2
0.7771	Intermediate Similarity	NPD1653	Approved
0.7766	Intermediate Similarity	NPD7435	Discontinued
0.7753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6801	Discontinued
0.7692	Intermediate Similarity	NPD7699	Phase 2
0.7692	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD7700	Phase 2
0.768	Intermediate Similarity	NPD6234	Discontinued
0.7661	Intermediate Similarity	NPD1549	Phase 2
0.7629	Intermediate Similarity	NPD6535	Approved
0.7629	Intermediate Similarity	NPD6534	Approved
0.7626	Intermediate Similarity	NPD6823	Phase 2
0.7624	Intermediate Similarity	NPD3749	Approved
0.7624	Intermediate Similarity	NPD7874	Approved
0.7624	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7685	Pre-registration
0.7606	Intermediate Similarity	NPD7240	Approved
0.7598	Intermediate Similarity	NPD37	Approved
0.7586	Intermediate Similarity	NPD7801	Approved
0.7569	Intermediate Similarity	NPD4965	Approved
0.7569	Intermediate Similarity	NPD4967	Phase 2
0.7569	Intermediate Similarity	NPD4966	Approved
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1247	Approved
0.7463	Intermediate Similarity	NPD8319	Approved
0.7463	Intermediate Similarity	NPD8320	Phase 1
0.7443	Intermediate Similarity	NPD7390	Discontinued
0.7419	Intermediate Similarity	NPD3926	Phase 2
0.7416	Intermediate Similarity	NPD5403	Approved
0.7398	Intermediate Similarity	NPD6213	Phase 3
0.7398	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6212	Phase 3
0.7384	Intermediate Similarity	NPD1510	Phase 2
0.7353	Intermediate Similarity	NPD1613	Approved
0.7353	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6799	Approved
0.7345	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2796	Approved
0.7327	Intermediate Similarity	NPD7680	Approved
0.732	Intermediate Similarity	NPD8150	Discontinued
0.7304	Intermediate Similarity	NPD7584	Approved
0.7303	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5401	Approved
0.7297	Intermediate Similarity	NPD919	Approved
0.7293	Intermediate Similarity	NPD6599	Discontinued
0.7251	Intermediate Similarity	NPD943	Approved
0.7241	Intermediate Similarity	NPD2935	Discontinued
0.7238	Intermediate Similarity	NPD7458	Discontinued
0.7232	Intermediate Similarity	NPD6190	Approved
0.7216	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2532	Approved
0.7207	Intermediate Similarity	NPD2533	Approved
0.7207	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD7266	Discontinued
0.72	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3750	Approved
0.7151	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7119	Intermediate Similarity	NPD6674	Discontinued
0.7119	Intermediate Similarity	NPD2800	Approved
0.7118	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8059	Phase 3
0.7087	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4628	Phase 3
0.7079	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3027	Phase 3
0.7069	Intermediate Similarity	NPD1607	Approved
0.7062	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD920	Approved
0.7017	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1933	Approved
0.7011	Intermediate Similarity	NPD230	Phase 1
0.701	Intermediate Similarity	NPD5953	Discontinued
0.6959	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5404	Approved
0.6949	Remote Similarity	NPD5405	Approved
0.6949	Remote Similarity	NPD5406	Approved
0.6949	Remote Similarity	NPD1551	Phase 2
0.6949	Remote Similarity	NPD5408	Approved
0.6947	Remote Similarity	NPD8127	Discontinued
0.6939	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7585	Approved
0.6931	Remote Similarity	NPD4363	Phase 3
0.6931	Remote Similarity	NPD4360	Phase 2
0.6919	Remote Similarity	NPD4908	Phase 1
0.6914	Remote Similarity	NPD447	Suspended
0.6911	Remote Similarity	NPD7229	Phase 3
0.691	Remote Similarity	NPD2346	Discontinued
0.691	Remote Similarity	NPD2344	Approved
0.6907	Remote Similarity	NPD7286	Phase 2
0.6906	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7930	Approved
0.6893	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2799	Discontinued
0.6893	Remote Similarity	NPD3748	Approved
0.6893	Remote Similarity	NPD651	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7583	Approved
0.6853	Remote Similarity	NPD7549	Discontinued
0.6839	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2313	Discontinued
0.6833	Remote Similarity	NPD1243	Approved
0.6823	Remote Similarity	NPD5711	Approved
0.6823	Remote Similarity	NPD5710	Approved
0.6816	Remote Similarity	NPD4287	Approved
0.6784	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6651	Approved
0.6769	Remote Similarity	NPD7177	Discontinued
0.676	Remote Similarity	NPD6099	Approved
0.676	Remote Similarity	NPD6100	Approved
0.6758	Remote Similarity	NPD2309	Approved
0.6755	Remote Similarity	NPD6844	Discontinued
0.6742	Remote Similarity	NPD7097	Phase 1
0.6712	Remote Similarity	NPD7907	Approved
0.6706	Remote Similarity	NPD1091	Approved
0.6705	Remote Similarity	NPD6233	Phase 2
0.6703	Remote Similarity	NPD7003	Approved
0.6703	Remote Similarity	NPD8166	Discontinued
0.6703	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5242	Approved
0.6699	Remote Similarity	NPD5006	Approved
0.6699	Remote Similarity	NPD5005	Approved
0.6697	Remote Similarity	NPD4665	Approved
0.6697	Remote Similarity	NPD4111	Phase 1

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