NPASS Compound

Structure

NPC12461 OpenBabel07101719512D 32 36 0 0 1 0 0 0 0 0999 V2000 2.4392 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8082 -2.3827 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 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 -4.3301 2.5000 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 -2.5981 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 -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 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 -5.1962 3.0000 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 1.0000 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 -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 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 -5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -3.4641 -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 25 1 0 0 0 0 2 25 1 0 0 0 0 4 30 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 25 1 0 0 0 0 9 26 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 19 2 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 24 2 0 0 0 0 16 17 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 23 1 0 0 0 0 18 29 2 0 0 0 0 19 31 1 0 0 0 0 20 30 1 0 0 0 0 21 23 2 0 0 0 0 21 31 1 0 0 0 0 22 25 1 0 0 0 0 22 26 1 6 0 0 0 23 24 1 0 0 0 0 24 32 1 0 0 0 0 26 3 1 1 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	447.119
LogP:	6.114
LogD:	3.7
LogS:	-3.482
# Rotatable Bonds:	2
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	3.796
Fsp3:	0.423
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.741
MDCK Permeability:	1.4921840374881867e-05
Pgp-inhibitor:	0.768
Pgp-substrate:	0.107
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.083

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	95.74101257324219%
Volume Distribution (VD):	0.605
Pgp-substrate:	6.69230318069458%

ADMET: Metabolism

CYP1A2-inhibitor:	0.389
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.532
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.571
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.372
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	4.604
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.672
AMES Toxicity:	0.251
Rat Oral Acute Toxicity:	0.392
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.917
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.886
Respiratory Toxicity:	0.876

Download Data

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

Natural Product: NPC12461

Natural Product ID:	NPC12461
*Common Name:**	Ugonin L
IUPAC Name:	(7aS,11aR)-3-(3,4-dihydroxyphenyl)-6-methoxy-8,8,11a-trimethyl-7a,9,10,11-tetrahydro-7H-pyrano[2,3-c]xanthen-1-one
Synonyms:	Ugonin L
Standard InCHIKey:	DVUORASKJFBCTF-BKMJKUGQSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-25(2)8-5-9-26(3)22(25)11-15-20(30-4)13-21-23(24(15)32-26)18(29)12-19(31-21)14-6-7-16(27)17(28)10-14/h6-7,10,12-13,22,27-28H,5,8-9,11H2,1-4H3/t22-,26+/m0/s1
SMILES:	CC1(C)CCC[C@]2(C)[C@H]1Cc1c(cc3c(c(=O)cc(c4ccc(c(c4)O)O)o3)c1O2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550368
PubChem CID:	10365741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003503] 6-prenylated flavones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19583252]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[28169537]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11959	Helminthostachys zeylanica	Species	Ophioglossaceae	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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[525416]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[525416]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	10100.0	nM	PMID[525417]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3800.0	nM	PMID[525416]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5800.0	nM	PMID[525416]

☑ 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 NPC12461 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	454
0.1-0.2	1758
0.2-0.3	3428
0.3-0.4	8889
0.4-0.5	9649
0.5-0.6	3948
0.6-0.7	5238
0.7-0.8	5245
0.8-0.85	2701
0.85-0.9	1204
0.9-0.95	171
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC206605
0.9805	High Similarity	NPC476280
0.9805	High Similarity	NPC297212
0.974	High Similarity	NPC46736
0.9618	High Similarity	NPC476295
0.9613	High Similarity	NPC197856
0.956	High Similarity	NPC476306
0.943	High Similarity	NPC474162
0.943	High Similarity	NPC474150
0.9371	High Similarity	NPC186686
0.9367	High Similarity	NPC57715
0.9367	High Similarity	NPC472906
0.9367	High Similarity	NPC472275
0.9367	High Similarity	NPC234644
0.9367	High Similarity	NPC32694
0.9359	High Similarity	NPC3980
0.9355	High Similarity	NPC170492
0.9313	High Similarity	NPC472450
0.9313	High Similarity	NPC275780
0.9313	High Similarity	NPC156432
0.9313	High Similarity	NPC239752
0.9308	High Similarity	NPC329760
0.9308	High Similarity	NPC78332
0.9304	High Similarity	NPC235018
0.9304	High Similarity	NPC188433
0.9304	High Similarity	NPC192686
0.9304	High Similarity	NPC28241
0.9304	High Similarity	NPC471973
0.9304	High Similarity	NPC45146
0.9304	High Similarity	NPC80375
0.9304	High Similarity	NPC119209
0.9304	High Similarity	NPC476283
0.9304	High Similarity	NPC118256
0.9299	High Similarity	NPC471209
0.9286	High Similarity	NPC3825
0.9286	High Similarity	NPC88804
0.9259	High Similarity	NPC300307
0.9259	High Similarity	NPC288813
0.9255	High Similarity	NPC43319
0.9255	High Similarity	NPC39091
0.9255	High Similarity	NPC320741
0.9255	High Similarity	NPC472449
0.9255	High Similarity	NPC171985
0.925	High Similarity	NPC23298
0.925	High Similarity	NPC306321
0.925	High Similarity	NPC189473
0.925	High Similarity	NPC303460
0.925	High Similarity	NPC207690
0.925	High Similarity	NPC220313
0.9245	High Similarity	NPC474038
0.9241	High Similarity	NPC235448
0.9241	High Similarity	NPC210459
0.9241	High Similarity	NPC185258
0.9241	High Similarity	NPC204879
0.9241	High Similarity	NPC172770
0.9236	High Similarity	NPC24640
0.9236	High Similarity	NPC471985
0.9236	High Similarity	NPC276444
0.9236	High Similarity	NPC282307
0.9236	High Similarity	NPC170026
0.9231	High Similarity	NPC213896
0.9231	High Similarity	NPC74924
0.9231	High Similarity	NPC192083
0.9226	High Similarity	NPC154345
0.9226	High Similarity	NPC305965
0.9198	High Similarity	NPC218226
0.9193	High Similarity	NPC293319
0.9187	High Similarity	NPC83922
0.9187	High Similarity	NPC194427
0.9187	High Similarity	NPC229632
0.9187	High Similarity	NPC472448
0.9182	High Similarity	NPC36217
0.9182	High Similarity	NPC204290
0.9182	High Similarity	NPC321399
0.9182	High Similarity	NPC475784
0.9182	High Similarity	NPC474960
0.9177	High Similarity	NPC284820
0.9177	High Similarity	NPC27337
0.9177	High Similarity	NPC52889
0.9177	High Similarity	NPC187745
0.9177	High Similarity	NPC219867
0.9177	High Similarity	NPC273843
0.9177	High Similarity	NPC476630
0.9177	High Similarity	NPC79053
0.9177	High Similarity	NPC304008
0.9177	High Similarity	NPC474681
0.9177	High Similarity	NPC180011
0.9177	High Similarity	NPC218313
0.9177	High Similarity	NPC473272
0.9177	High Similarity	NPC136674
0.9177	High Similarity	NPC237418
0.9177	High Similarity	NPC218871
0.9177	High Similarity	NPC161960
0.9172	High Similarity	NPC67396
0.9172	High Similarity	NPC321779
0.9172	High Similarity	NPC133392
0.9172	High Similarity	NPC234255
0.9167	High Similarity	NPC106976
0.9167	High Similarity	NPC63187
0.9167	High Similarity	NPC157784
0.9167	High Similarity	NPC37684
0.9167	High Similarity	NPC471982
0.9146	High Similarity	NPC4200
0.9141	High Similarity	NPC165456
0.9141	High Similarity	NPC107627
0.9141	High Similarity	NPC476637
0.9141	High Similarity	NPC188079
0.9136	High Similarity	NPC37870
0.9136	High Similarity	NPC272502
0.9136	High Similarity	NPC224851
0.9136	High Similarity	NPC120593
0.913	High Similarity	NPC236521
0.913	High Similarity	NPC472625
0.913	High Similarity	NPC248638
0.913	High Similarity	NPC152659
0.9125	High Similarity	NPC198829
0.9125	High Similarity	NPC472632
0.9125	High Similarity	NPC61010
0.9125	High Similarity	NPC471210
0.9125	High Similarity	NPC167678
0.9125	High Similarity	NPC187354
0.9125	High Similarity	NPC278427
0.9125	High Similarity	NPC142252
0.9125	High Similarity	NPC26326
0.9125	High Similarity	NPC29876
0.9119	High Similarity	NPC184755
0.9119	High Similarity	NPC53545
0.9119	High Similarity	NPC85121
0.9119	High Similarity	NPC117418
0.9119	High Similarity	NPC74178
0.9114	High Similarity	NPC115853
0.9114	High Similarity	NPC291878
0.9114	High Similarity	NPC195796
0.9114	High Similarity	NPC5322
0.9114	High Similarity	NPC472455
0.9114	High Similarity	NPC35038
0.9114	High Similarity	NPC475799
0.9114	High Similarity	NPC6633
0.9114	High Similarity	NPC133970
0.9114	High Similarity	NPC278778
0.9114	High Similarity	NPC142339
0.9114	High Similarity	NPC13779
0.9108	High Similarity	NPC298692
0.9103	High Similarity	NPC304295
0.9103	High Similarity	NPC205046
0.9103	High Similarity	NPC59162
0.9091	High Similarity	NPC108406
0.9085	High Similarity	NPC472276
0.9085	High Similarity	NPC101107
0.9074	High Similarity	NPC303174
0.9074	High Similarity	NPC473286
0.9074	High Similarity	NPC472277
0.9074	High Similarity	NPC62261
0.9068	High Similarity	NPC201800
0.9068	High Similarity	NPC474034
0.9068	High Similarity	NPC474033
0.9068	High Similarity	NPC25152
0.9068	High Similarity	NPC476247
0.9068	High Similarity	NPC470694
0.9062	High Similarity	NPC328102
0.9062	High Similarity	NPC56085
0.9062	High Similarity	NPC228785
0.9062	High Similarity	NPC476980
0.9062	High Similarity	NPC14353
0.9062	High Similarity	NPC174953
0.9062	High Similarity	NPC139036
0.9062	High Similarity	NPC472624
0.9057	High Similarity	NPC236796
0.9057	High Similarity	NPC474055
0.9057	High Similarity	NPC78225
0.9057	High Similarity	NPC299520
0.9057	High Similarity	NPC129684
0.9057	High Similarity	NPC472963
0.9057	High Similarity	NPC472598
0.9057	High Similarity	NPC291508
0.9051	High Similarity	NPC230149
0.9051	High Similarity	NPC152951
0.9051	High Similarity	NPC256925
0.9051	High Similarity	NPC477503
0.9051	High Similarity	NPC113906
0.9051	High Similarity	NPC168247
0.9051	High Similarity	NPC57674
0.9051	High Similarity	NPC117992
0.9051	High Similarity	NPC472280
0.9051	High Similarity	NPC56786
0.9051	High Similarity	NPC80534
0.9051	High Similarity	NPC45849
0.9051	High Similarity	NPC200761
0.9051	High Similarity	NPC200246
0.9051	High Similarity	NPC470327
0.9045	High Similarity	NPC249570
0.9045	High Similarity	NPC472912
0.9045	High Similarity	NPC237994
0.9045	High Similarity	NPC260979
0.9038	High Similarity	NPC472633
0.9038	High Similarity	NPC29777
0.9038	High Similarity	NPC471115
0.9032	High Similarity	NPC3036
0.9024	High Similarity	NPC475805
0.9024	High Similarity	NPC475212

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 NPC12461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	962
0.2-0.3	1659
0.3-0.4	2672
0.4-0.5	1938
0.5-0.6	948
0.6-0.7	394
0.7-0.8	135
0.8-0.85	33
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD2393	Clinical (unspecified phase)
0.8924	High Similarity	NPD1934	Approved
0.8896	High Similarity	NPD1511	Approved
0.8868	High Similarity	NPD2801	Approved
0.8841	High Similarity	NPD6168	Clinical (unspecified phase)
0.8841	High Similarity	NPD6167	Clinical (unspecified phase)
0.8841	High Similarity	NPD6166	Phase 2
0.8782	High Similarity	NPD1512	Approved
0.8718	High Similarity	NPD4378	Clinical (unspecified phase)
0.8599	High Similarity	NPD7410	Clinical (unspecified phase)
0.858	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD7054	Approved
0.8562	High Similarity	NPD4380	Phase 2
0.8545	High Similarity	NPD6959	Discontinued
0.8521	High Similarity	NPD7074	Phase 3
0.8521	High Similarity	NPD7472	Approved
0.8485	Intermediate Similarity	NPD5494	Approved
0.8471	Intermediate Similarity	NPD6797	Phase 2
0.8452	Intermediate Similarity	NPD7473	Discontinued
0.8421	Intermediate Similarity	NPD7251	Discontinued
0.8415	Intermediate Similarity	NPD3882	Suspended
0.8415	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7819	Suspended
0.8383	Intermediate Similarity	NPD6232	Discontinued
0.8354	Intermediate Similarity	NPD3817	Phase 2
0.8294	Intermediate Similarity	NPD3818	Discontinued
0.8282	Intermediate Similarity	NPD7411	Suspended
0.8269	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7808	Phase 3
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7075	Discontinued
0.8246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD5844	Phase 1
0.8217	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.8101	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6100	Approved
0.8089	Intermediate Similarity	NPD6099	Approved
0.8089	Intermediate Similarity	NPD2796	Approved
0.8072	Intermediate Similarity	NPD1465	Phase 2
0.805	Intermediate Similarity	NPD2800	Approved
0.8046	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD3749	Approved
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.7976	Intermediate Similarity	NPD7768	Phase 2
0.7898	Intermediate Similarity	NPD1607	Approved
0.7885	Intermediate Similarity	NPD943	Approved
0.7853	Intermediate Similarity	NPD6799	Approved
0.7853	Intermediate Similarity	NPD7390	Discontinued
0.7805	Intermediate Similarity	NPD2533	Approved
0.7805	Intermediate Similarity	NPD2532	Approved
0.7805	Intermediate Similarity	NPD2534	Approved
0.7797	Intermediate Similarity	NPD6559	Discontinued
0.7785	Intermediate Similarity	NPD6651	Approved
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2935	Discontinued
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3226	Approved
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5402	Approved
0.7705	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1247	Approved
0.7688	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3748	Approved
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD919	Approved
0.767	Intermediate Similarity	NPD3751	Discontinued
0.7658	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1613	Approved
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD3787	Discontinued
0.7628	Intermediate Similarity	NPD4908	Phase 1
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8312	Approved
0.7611	Intermediate Similarity	NPD8313	Approved
0.7605	Intermediate Similarity	NPD5403	Approved
0.76	Intermediate Similarity	NPD3926	Phase 2
0.7593	Intermediate Similarity	NPD2346	Discontinued
0.759	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.7578	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7572	Intermediate Similarity	NPD6234	Discontinued
0.7571	Intermediate Similarity	NPD7228	Approved
0.7561	Intermediate Similarity	NPD4628	Phase 3
0.7527	Intermediate Similarity	NPD4360	Phase 2
0.7527	Intermediate Similarity	NPD4363	Phase 3
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.7513	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD4625	Phase 3
0.7455	Intermediate Similarity	NPD8166	Discontinued
0.7455	Intermediate Similarity	NPD7003	Approved
0.7423	Intermediate Similarity	NPD1551	Phase 2
0.7421	Intermediate Similarity	NPD6781	Approved
0.7421	Intermediate Similarity	NPD6777	Approved
0.7421	Intermediate Similarity	NPD2313	Discontinued
0.7421	Intermediate Similarity	NPD6779	Approved
0.7421	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD6780	Approved
0.7421	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6782	Approved
0.7412	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7384	Intermediate Similarity	NPD37	Approved
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2344	Approved
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3027	Phase 3
0.7356	Intermediate Similarity	NPD4967	Phase 2
0.7356	Intermediate Similarity	NPD4966	Approved
0.7356	Intermediate Similarity	NPD4965	Approved
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.7345	Intermediate Similarity	NPD5710	Approved
0.7345	Intermediate Similarity	NPD5711	Approved
0.7333	Intermediate Similarity	NPD7286	Phase 2
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3268	Approved
0.7312	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7685	Pre-registration
0.7306	Intermediate Similarity	NPD7435	Discontinued
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD1610	Phase 2
0.7284	Intermediate Similarity	NPD5124	Phase 1
0.7284	Intermediate Similarity	NPD447	Suspended
0.7284	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2798	Approved
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5760	Phase 2
0.7241	Intermediate Similarity	NPD5761	Phase 2
0.7235	Intermediate Similarity	NPD6273	Approved
0.7222	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD7698	Approved
0.7216	Intermediate Similarity	NPD7697	Approved
0.7215	Intermediate Similarity	NPD2797	Approved
0.7212	Intermediate Similarity	NPD5408	Approved
0.7212	Intermediate Similarity	NPD5404	Approved
0.7212	Intermediate Similarity	NPD5405	Approved
0.7212	Intermediate Similarity	NPD5406	Approved
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2309	Approved
0.7202	Intermediate Similarity	NPD6190	Approved
0.7197	Intermediate Similarity	NPD4749	Approved
0.7194	Intermediate Similarity	NPD7584	Approved
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7179	Intermediate Similarity	NPD7870	Phase 2
0.7179	Intermediate Similarity	NPD7871	Phase 2
0.7179	Intermediate Similarity	NPD1201	Approved
0.7178	Intermediate Similarity	NPD1933	Approved
0.7174	Intermediate Similarity	NPD7549	Discontinued
0.7165	Intermediate Similarity	NPD6823	Phase 2
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD1653	Approved
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7136	Intermediate Similarity	NPD7801	Approved
0.7134	Intermediate Similarity	NPD1608	Approved
0.7128	Intermediate Similarity	NPD4287	Approved
0.7126	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7240	Approved
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7113	Intermediate Similarity	NPD2494	Approved
0.7113	Intermediate Similarity	NPD2493	Approved
0.7107	Intermediate Similarity	NPD1470	Approved
0.7107	Intermediate Similarity	NPD1203	Approved
0.7102	Intermediate Similarity	NPD4288	Approved
0.7092	Intermediate Similarity	NPD4582	Approved
0.7092	Intermediate Similarity	NPD4583	Approved
0.7089	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7874	Approved
0.7085	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2403	Approved
0.707	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3300	Phase 2
0.7048	Intermediate Similarity	NPD4308	Phase 3
0.7047	Intermediate Similarity	NPD7699	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