NPASS Compound

Structure

CID136674 OpenBabel06191715492D 29 31 0 0 0 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 3.8660 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 -5.1962 2.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -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 0.8660 0.5000 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 1.7321 -1.0000 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 -1.7321 3.0000 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 3.4641 2.0000 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 23 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 13 18 2 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 22 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.17
Volume:	412.344
LogP:	4.825
LogD:	2.742
LogS:	-3.208
# Rotatable Bonds:	5
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	3.146
Fsp3:	0.348
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:	-4.836
MDCK Permeability:	1.2939727639604826e-05
Pgp-inhibitor:	0.139
Pgp-substrate:	0.057
Human Intestinal Absorption (HIA):	0.235
20% Bioavailability (F20%):	0.272
30% Bioavailability (F30%):	0.174

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	92.97483825683594%
Volume Distribution (VD):	0.83
Pgp-substrate:	9.023721694946289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.768
CYP1A2-substrate:	0.404
CYP2C19-inhibitor:	0.553
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.755
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.535
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.132
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	5.883
Half-life (T1/2):	0.629

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.588
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.623
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.091
Skin Sensitization:	0.85
Carcinogencity:	0.118
Eye Corrosion:	0.003
Eye Irritation:	0.664
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC136674

Natural Product ID:	NPC136674
*Common Name:**	Nigrolineaxanthone N
IUPAC Name:	1,3,5-trihydroxy-8-(3-hydroxy-3-methylbutyl)-2-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	Nigrolineaxanthone N
Standard InCHIKey:	ZPJQIAIELUCBCV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H26O6/c1-12(2)5-7-14-16(25)11-17-19(20(14)26)21(27)18-13(9-10-23(3,4)28)6-8-15(24)22(18)29-17/h5-6,8,11,24-26,28H,7,9-10H2,1-4H3
SMILES:	CC(=CCc1c(O)cc2c(c1O)c(=O)c1c(o2)c(O)ccc1CCC(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL408716
PubChem CID:	5323589
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 [CHEMONTID:0003519] 8-prenylated 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
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[14695790]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[16124764]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[518016]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[518017]

☑ 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 NPC136674 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	458
0.1-0.2	1895
0.2-0.3	4453
0.3-0.4	11037
0.4-0.5	6784
0.5-0.6	3648
0.6-0.7	5085
0.7-0.8	4984
0.8-0.85	2515
0.85-0.9	1219
0.9-0.95	553
0.95-1	66

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC471973
0.9801	High Similarity	NPC235448
0.9675	High Similarity	NPC23298
0.9675	High Similarity	NPC189473
0.9673	High Similarity	NPC61010
0.9671	High Similarity	NPC100123
0.9669	High Similarity	NPC472907
0.9667	High Similarity	NPC49402
0.9667	High Similarity	NPC227337
0.9667	High Similarity	NPC273462
0.9667	High Similarity	NPC70433
0.9667	High Similarity	NPC33051
0.9667	High Similarity	NPC472905
0.9613	High Similarity	NPC472450
0.9613	High Similarity	NPC239752
0.9613	High Similarity	NPC275780
0.961	High Similarity	NPC25152
0.9608	High Similarity	NPC56085
0.9608	High Similarity	NPC14353
0.9608	High Similarity	NPC228785
0.9608	High Similarity	NPC320359
0.9608	High Similarity	NPC36217
0.9605	High Similarity	NPC218313
0.9605	High Similarity	NPC304008
0.9605	High Similarity	NPC472963
0.9605	High Similarity	NPC474681
0.9605	High Similarity	NPC161960
0.9605	High Similarity	NPC187745
0.9603	High Similarity	NPC472280
0.9603	High Similarity	NPC230149
0.9603	High Similarity	NPC168247
0.9603	High Similarity	NPC57674
0.9603	High Similarity	NPC117992
0.9603	High Similarity	NPC256925
0.9603	High Similarity	NPC152951
0.9597	High Similarity	NPC151473
0.9551	High Similarity	NPC37870
0.9551	High Similarity	NPC472449
0.9551	High Similarity	NPC39091
0.9548	High Similarity	NPC152659
0.9548	High Similarity	NPC248638
0.9548	High Similarity	NPC186686
0.9548	High Similarity	NPC236521
0.9548	High Similarity	NPC220313
0.9545	High Similarity	NPC278052
0.9545	High Similarity	NPC234644
0.9545	High Similarity	NPC40491
0.9542	High Similarity	NPC204879
0.9542	High Similarity	NPC476242
0.9539	High Similarity	NPC133970
0.9539	High Similarity	NPC274730
0.9539	High Similarity	NPC115853
0.9539	High Similarity	NPC470600
0.9539	High Similarity	NPC6633
0.9539	High Similarity	NPC191146
0.9539	High Similarity	NPC472455
0.9539	High Similarity	NPC5322
0.9539	High Similarity	NPC68093
0.9539	High Similarity	NPC142339
0.9487	High Similarity	NPC293319
0.9484	High Similarity	NPC229632
0.9484	High Similarity	NPC201800
0.9484	High Similarity	NPC329760
0.9484	High Similarity	NPC474150
0.9484	High Similarity	NPC474162
0.9481	High Similarity	NPC139036
0.9481	High Similarity	NPC204290
0.9481	High Similarity	NPC474960
0.9481	High Similarity	NPC45146
0.9481	High Similarity	NPC235018
0.9481	High Similarity	NPC80375
0.9481	High Similarity	NPC200746
0.9481	High Similarity	NPC188433
0.9477	High Similarity	NPC78225
0.9477	High Similarity	NPC217677
0.9477	High Similarity	NPC219867
0.9477	High Similarity	NPC241904
0.9477	High Similarity	NPC236796
0.9477	High Similarity	NPC27337
0.9477	High Similarity	NPC165977
0.9477	High Similarity	NPC180011
0.9477	High Similarity	NPC300727
0.9474	High Similarity	NPC234255
0.9474	High Similarity	NPC200246
0.947	High Similarity	NPC237994
0.9427	High Similarity	NPC170245
0.9427	High Similarity	NPC43319
0.9423	High Similarity	NPC146134
0.9423	High Similarity	NPC7483
0.9423	High Similarity	NPC207690
0.9423	High Similarity	NPC236132
0.9419	High Similarity	NPC474187
0.9419	High Similarity	NPC57715
0.9419	High Similarity	NPC32694
0.9419	High Similarity	NPC167678
0.9419	High Similarity	NPC472906
0.9419	High Similarity	NPC29876
0.9416	High Similarity	NPC474290
0.9416	High Similarity	NPC210459
0.9412	High Similarity	NPC138243
0.9412	High Similarity	NPC195796
0.9412	High Similarity	NPC278778
0.9412	High Similarity	NPC291878
0.9412	High Similarity	NPC24640
0.9412	High Similarity	NPC471985
0.9412	High Similarity	NPC35038
0.9408	High Similarity	NPC89474
0.9404	High Similarity	NPC154345
0.9367	High Similarity	NPC477154
0.9367	High Similarity	NPC6588
0.9367	High Similarity	NPC117854
0.9367	High Similarity	NPC218226
0.9363	High Similarity	NPC303174
0.9363	High Similarity	NPC326520
0.9363	High Similarity	NPC62261
0.9359	High Similarity	NPC472964
0.9359	High Similarity	NPC472448
0.9359	High Similarity	NPC83922
0.9355	High Similarity	NPC476980
0.9355	High Similarity	NPC474287
0.9355	High Similarity	NPC119209
0.9355	High Similarity	NPC119224
0.9355	High Similarity	NPC192686
0.9355	High Similarity	NPC472902
0.9355	High Similarity	NPC118256
0.9355	High Similarity	NPC299436
0.9355	High Similarity	NPC475886
0.9355	High Similarity	NPC472624
0.9355	High Similarity	NPC321399
0.9351	High Similarity	NPC291508
0.9351	High Similarity	NPC273843
0.9351	High Similarity	NPC262286
0.9351	High Similarity	NPC299520
0.9351	High Similarity	NPC474055
0.9351	High Similarity	NPC36852
0.9351	High Similarity	NPC52889
0.9351	High Similarity	NPC129684
0.9351	High Similarity	NPC472598
0.9346	High Similarity	NPC67396
0.9346	High Similarity	NPC477503
0.9346	High Similarity	NPC470327
0.9346	High Similarity	NPC45849
0.9346	High Similarity	NPC200761
0.9342	High Similarity	NPC260979
0.9342	High Similarity	NPC257648
0.9342	High Similarity	NPC471982
0.9342	High Similarity	NPC472912
0.9342	High Similarity	NPC477231
0.9338	High Similarity	NPC29231
0.9338	High Similarity	NPC3825
0.9338	High Similarity	NPC88804
0.9333	High Similarity	NPC43669
0.9333	High Similarity	NPC272721
0.9333	High Similarity	NPC196277
0.9304	High Similarity	NPC235610
0.9299	High Similarity	NPC303460
0.9299	High Similarity	NPC319200
0.9299	High Similarity	NPC306321
0.9299	High Similarity	NPC41301
0.9299	High Similarity	NPC270837
0.9299	High Similarity	NPC475985
0.9299	High Similarity	NPC187491
0.9299	High Similarity	NPC124038
0.9295	High Similarity	NPC472634
0.9295	High Similarity	NPC471210
0.9295	High Similarity	NPC474351
0.9295	High Similarity	NPC472632
0.9295	High Similarity	NPC259456
0.9295	High Similarity	NPC474186
0.9295	High Similarity	NPC474038
0.9295	High Similarity	NPC266314
0.9295	High Similarity	NPC475883
0.9295	High Similarity	NPC134783
0.929	High Similarity	NPC55738
0.929	High Similarity	NPC250214
0.929	High Similarity	NPC184755
0.929	High Similarity	NPC280680
0.929	High Similarity	NPC172770
0.929	High Similarity	NPC74178
0.929	High Similarity	NPC185258
0.929	High Similarity	NPC95936
0.929	High Similarity	NPC85121
0.9286	High Similarity	NPC475799
0.9286	High Similarity	NPC13779
0.9286	High Similarity	NPC209614
0.9286	High Similarity	NPC472626
0.9286	High Similarity	NPC470328
0.9281	High Similarity	NPC213896
0.9281	High Similarity	NPC170492
0.9281	High Similarity	NPC18727
0.9281	High Similarity	NPC469550
0.9281	High Similarity	NPC192083
0.9281	High Similarity	NPC74924
0.9276	High Similarity	NPC31363
0.9276	High Similarity	NPC202157
0.9272	High Similarity	NPC65775
0.9272	High Similarity	NPC10027
0.9267	High Similarity	NPC77378
0.9245	High Similarity	NPC476306
0.9245	High Similarity	NPC474024

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 NPC136674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1023
0.2-0.3	1721
0.3-0.4	2693
0.4-0.5	1761
0.5-0.6	967
0.6-0.7	394
0.7-0.8	128
0.8-0.85	35
0.85-0.9	12
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD2393	Clinical (unspecified phase)
0.9216	High Similarity	NPD1934	Approved
0.9156	High Similarity	NPD2801	Approved
0.894	High Similarity	NPD1511	Approved
0.8917	High Similarity	NPD3882	Suspended
0.8824	High Similarity	NPD1512	Approved
0.8765	High Similarity	NPD6166	Phase 2
0.8765	High Similarity	NPD6168	Clinical (unspecified phase)
0.8765	High Similarity	NPD6167	Clinical (unspecified phase)
0.8758	High Similarity	NPD6232	Discontinued
0.8712	High Similarity	NPD7473	Discontinued
0.8671	High Similarity	NPD7819	Suspended
0.8636	High Similarity	NPD4378	Clinical (unspecified phase)
0.8634	High Similarity	NPD5494	Approved
0.8554	High Similarity	NPD7074	Phase 3
0.8553	High Similarity	NPD1465	Phase 2
0.8545	High Similarity	NPD3818	Discontinued
0.8516	High Similarity	NPD7410	Clinical (unspecified phase)
0.8509	High Similarity	NPD7075	Discontinued
0.85	High Similarity	NPD3817	Phase 2
0.8494	Intermediate Similarity	NPD7054	Approved
0.8481	Intermediate Similarity	NPD4380	Phase 2
0.8447	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7472	Approved
0.8438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD5844	Phase 1
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6797	Phase 2
0.8282	Intermediate Similarity	NPD3749	Approved
0.8267	Intermediate Similarity	NPD943	Approved
0.8235	Intermediate Similarity	NPD7251	Discontinued
0.8199	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD7808	Phase 3
0.8171	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1510	Phase 2
0.8148	Intermediate Similarity	NPD6801	Discontinued
0.8146	Intermediate Similarity	NPD1240	Approved
0.8141	Intermediate Similarity	NPD3750	Approved
0.8129	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2796	Approved
0.8101	Intermediate Similarity	NPD6799	Approved
0.8077	Intermediate Similarity	NPD2800	Approved
0.8059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2534	Approved
0.805	Intermediate Similarity	NPD2533	Approved
0.805	Intermediate Similarity	NPD2532	Approved
0.8039	Intermediate Similarity	NPD1607	Approved
0.8036	Intermediate Similarity	NPD3926	Phase 2
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8011	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6099	Approved
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6100	Approved
0.7988	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD3226	Approved
0.7949	Intermediate Similarity	NPD2346	Discontinued
0.7935	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7917	Intermediate Similarity	NPD1247	Approved
0.7904	Intermediate Similarity	NPD919	Approved
0.7892	Intermediate Similarity	NPD7768	Phase 2
0.7829	Intermediate Similarity	NPD4625	Phase 3
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7821	Intermediate Similarity	NPD3748	Approved
0.7811	Intermediate Similarity	NPD7199	Phase 2
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6234	Discontinued
0.7792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1613	Approved
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7764	Intermediate Similarity	NPD7390	Discontinued
0.7742	Intermediate Similarity	NPD447	Suspended
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5402	Approved
0.7722	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3751	Discontinued
0.7688	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD230	Phase 1
0.7625	Intermediate Similarity	NPD1243	Approved
0.7622	Intermediate Similarity	NPD5403	Approved
0.7605	Intermediate Similarity	NPD37	Approved
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.7586	Intermediate Similarity	NPD7228	Approved
0.758	Intermediate Similarity	NPD6651	Approved
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7574	Intermediate Similarity	NPD4965	Approved
0.7574	Intermediate Similarity	NPD4967	Phase 2
0.7574	Intermediate Similarity	NPD4966	Approved
0.7571	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5711	Approved
0.7558	Intermediate Similarity	NPD5710	Approved
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2313	Discontinued
0.7548	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1551	Phase 2
0.7546	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2309	Approved
0.7528	Intermediate Similarity	NPD8313	Approved
0.7528	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD1933	Approved
0.7515	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD9494	Approved
0.7451	Intermediate Similarity	NPD1470	Approved
0.7443	Intermediate Similarity	NPD7286	Phase 2
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7417	Intermediate Similarity	NPD1201	Approved
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7229	Phase 3
0.7342	Intermediate Similarity	NPD4060	Phase 1
0.7338	Intermediate Similarity	NPD1203	Approved
0.7329	Intermediate Similarity	NPD5408	Approved
0.7329	Intermediate Similarity	NPD5405	Approved
0.7329	Intermediate Similarity	NPD5404	Approved
0.7329	Intermediate Similarity	NPD5406	Approved
0.7325	Intermediate Similarity	NPD3764	Approved
0.7325	Intermediate Similarity	NPD3268	Approved
0.7322	Intermediate Similarity	NPD4287	Approved
0.7321	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4749	Approved
0.7318	Intermediate Similarity	NPD7685	Pre-registration
0.7317	Intermediate Similarity	NPD6190	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7306	Intermediate Similarity	NPD8151	Discontinued
0.7303	Intermediate Similarity	NPD1610	Phase 2
0.729	Intermediate Similarity	NPD2798	Approved
0.7284	Intermediate Similarity	NPD1471	Phase 3
0.7262	Intermediate Similarity	NPD1653	Approved
0.7258	Intermediate Similarity	NPD4360	Phase 2
0.7258	Intermediate Similarity	NPD4363	Phase 3
0.7255	Intermediate Similarity	NPD1608	Approved
0.7231	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7783	Phase 2
0.7226	Intermediate Similarity	NPD2797	Approved
0.7225	Intermediate Similarity	NPD7697	Approved
0.7225	Intermediate Similarity	NPD7698	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD5242	Approved
0.7209	Intermediate Similarity	NPD4288	Approved
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2403	Approved
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.716	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7128	Intermediate Similarity	NPD4361	Phase 2
0.7128	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7240	Approved
0.712	Intermediate Similarity	NPD2494	Approved
0.712	Intermediate Similarity	NPD2493	Approved
0.7118	Intermediate Similarity	NPD7458	Discontinued
0.7113	Intermediate Similarity	NPD7584	Approved
0.7107	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD422	Phase 1
0.7066	Intermediate Similarity	NPD3300	Phase 2
0.7059	Intermediate Similarity	NPD17	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