NPASS Compound

Structure

NPC476170 OpenBabel07101718192D 32 37 0 0 1 0 0 0 0 0999 V2000 -1.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -3.3660 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 -2.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9394 -1.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3571 -1.7406 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3516 -1.8452 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 -6.5327 -0.1226 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 -4.9504 -0.8271 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 -0.8660 -1.5000 0.0000 C 0 0 2 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 -5.5382 -0.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1314 0.8955 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 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 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 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7584 -2.7587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1205 0.6864 0.0000 O 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 -5.7192 1.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9559 -0.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 26 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 13 27 1 0 0 0 0 14 21 2 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 31 1 0 0 0 0 17 24 1 0 0 0 0 17 25 1 1 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 20 23 1 0 0 0 0 20 29 2 0 0 0 0 21 32 1 0 0 0 0 22 23 2 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 25 3 1 6 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.14
Volume:	427.421
LogP:	5.789
LogD:	3.518
LogS:	-5.007
# Rotatable Bonds:	0
TPSA:	113.27
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	4.354
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.961
MDCK Permeability:	1.3477551874530036e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.141
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.3

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	87.64000701904297%
Volume Distribution (VD):	0.897
Pgp-substrate:	16.898900985717773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.842
CYP1A2-substrate:	0.65
CYP2C19-inhibitor:	0.444
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.249
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	4.617
Half-life (T1/2):	0.423

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.758
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.497
Rat Oral Acute Toxicity:	0.81
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.324
Carcinogencity:	0.804
Eye Corrosion:	0.003
Eye Irritation:	0.686
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC476170

Natural Product ID:	NPC476170
*Common Name:**	Ugonin O
IUPAC Name:	n.a.
Synonyms:	Ugonin O
Standard InCHIKey:	WYRBYPPKPYWQQK-NSYGIPOTSA-N
Standard InCHI:	InChI=1S/C25H22O7/c1-24(2)5-4-6-25(3)17(24)9-12-18-16(10-14(28)21(12)32-25)31-23-20(29)19-13(27)7-11(26)8-15(19)30-22(18)23/h4,6-8,10,17,26-28H,5,9H2,1-3H3/t17-,25+/m1/s1
SMILES:	CC1(C)CC=C[C@@]2(C)[C@@H]1Cc1c3c(cc(c1O2)O)oc1c(=O)c2c(cc(cc2oc31)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550505
PubChem CID:	44233938
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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	6

Activity Type	# Activity
Cell Line	4
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[558483]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[558483]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	7700.0	nM	PMID[558484]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3300.0	nM	PMID[558484]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3400.0	nM	PMID[558483]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3900.0	nM	PMID[558483]

☑ 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 NPC476170 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	499
0.1-0.2	1982
0.2-0.3	4246
0.3-0.4	10686
0.4-0.5	7699
0.5-0.6	4211
0.6-0.7	5898
0.7-0.8	5268
0.8-0.85	1540
0.85-0.9	638
0.9-0.95	26
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9704	High Similarity	NPC476273
0.9191	High Similarity	NPC23553
0.9191	High Similarity	NPC77179
0.9143	High Similarity	NPC246153
0.908	High Similarity	NPC221820
0.9064	High Similarity	NPC247136
0.9034	High Similarity	NPC240508
0.9034	High Similarity	NPC228209
0.9017	High Similarity	NPC149846
0.9006	High Similarity	NPC476306
0.9	High Similarity	NPC36320
0.9	High Similarity	NPC45449
0.8989	High Similarity	NPC240808
0.8988	High Similarity	NPC200746
0.8953	High Similarity	NPC202470
0.8947	High Similarity	NPC472449
0.8941	High Similarity	NPC59295
0.8941	High Similarity	NPC1706
0.8941	High Similarity	NPC1755
0.8941	High Similarity	NPC263092
0.8941	High Similarity	NPC133065
0.8941	High Similarity	NPC39305
0.8927	High Similarity	NPC8927
0.8908	High Similarity	NPC476640
0.8908	High Similarity	NPC473834
0.8908	High Similarity	NPC310794
0.8908	High Similarity	NPC30550
0.8908	High Similarity	NPC82217
0.8908	High Similarity	NPC216842
0.8902	High Similarity	NPC101107
0.8889	High Similarity	NPC39306
0.8889	High Similarity	NPC224280
0.8882	High Similarity	NPC312056
0.8882	High Similarity	NPC25152
0.8882	High Similarity	NPC272722
0.8882	High Similarity	NPC84515
0.8882	High Similarity	NPC238995
0.8876	High Similarity	NPC139036
0.8864	High Similarity	NPC246877
0.8857	High Similarity	NPC227906
0.8857	High Similarity	NPC287243
0.8851	High Similarity	NPC230619
0.8851	High Similarity	NPC54098
0.8844	High Similarity	NPC475805
0.8837	High Similarity	NPC477517
0.883	High Similarity	NPC248638
0.883	High Similarity	NPC220313
0.883	High Similarity	NPC152659
0.883	High Similarity	NPC23298
0.883	High Similarity	NPC146134
0.883	High Similarity	NPC236521
0.883	High Similarity	NPC189473
0.883	High Similarity	NPC475985
0.8824	High Similarity	NPC188486
0.8817	High Similarity	NPC474290
0.8817	High Similarity	NPC476242
0.8814	High Similarity	NPC104682
0.881	High Similarity	NPC274730
0.8807	High Similarity	NPC49667
0.8807	High Similarity	NPC8127
0.8793	High Similarity	NPC476641
0.8786	High Similarity	NPC126204
0.8786	High Similarity	NPC470704
0.8779	High Similarity	NPC275780
0.8779	High Similarity	NPC239752
0.8779	High Similarity	NPC472450
0.8779	High Similarity	NPC234052
0.8765	High Similarity	NPC80375
0.8765	High Similarity	NPC45146
0.8765	High Similarity	NPC235018
0.8757	High Similarity	NPC300727
0.8757	High Similarity	NPC241904
0.875	High Similarity	NPC245975
0.8743	High Similarity	NPC174700
0.8736	High Similarity	NPC60848
0.8736	High Similarity	NPC152477
0.8736	High Similarity	NPC476637
0.8728	High Similarity	NPC170245
0.8728	High Similarity	NPC39091
0.8728	High Similarity	NPC37870
0.8728	High Similarity	NPC277480
0.8721	High Similarity	NPC303460
0.8721	High Similarity	NPC306321
0.8715	High Similarity	NPC182693
0.8715	High Similarity	NPC471842
0.8715	High Similarity	NPC150977
0.8713	High Similarity	NPC173137
0.8713	High Similarity	NPC32694
0.8713	High Similarity	NPC61010
0.8713	High Similarity	NPC472906
0.8706	High Similarity	NPC16935
0.8706	High Similarity	NPC152904
0.8706	High Similarity	NPC100123
0.8706	High Similarity	NPC196879
0.8706	High Similarity	NPC280680
0.8706	High Similarity	NPC235448
0.8706	High Similarity	NPC195832
0.8698	High Similarity	NPC472461
0.8693	High Similarity	NPC65885
0.869	High Similarity	NPC89474
0.8686	High Similarity	NPC131866
0.8686	High Similarity	NPC28042
0.8686	High Similarity	NPC472276
0.8681	High Similarity	NPC295436
0.8678	High Similarity	NPC117854
0.8678	High Similarity	NPC247973
0.8678	High Similarity	NPC477154
0.8678	High Similarity	NPC6588
0.8671	High Similarity	NPC473286
0.8671	High Similarity	NPC62261
0.8671	High Similarity	NPC326520
0.8671	High Similarity	NPC37183
0.8671	High Similarity	NPC156432
0.8663	High Similarity	NPC206605
0.8663	High Similarity	NPC52204
0.8663	High Similarity	NPC329760
0.8663	High Similarity	NPC78332
0.8663	High Similarity	NPC229632
0.8659	High Similarity	NPC47883
0.8655	High Similarity	NPC14353
0.8655	High Similarity	NPC56085
0.8655	High Similarity	NPC204290
0.8655	High Similarity	NPC320359
0.8655	High Similarity	NPC471973
0.8655	High Similarity	NPC228785
0.8652	High Similarity	NPC98546
0.8652	High Similarity	NPC297807
0.8647	High Similarity	NPC472910
0.8647	High Similarity	NPC472913
0.8647	High Similarity	NPC245758
0.8647	High Similarity	NPC469584
0.8647	High Similarity	NPC222814
0.8647	High Similarity	NPC136674
0.8647	High Similarity	NPC96167
0.8647	High Similarity	NPC101830
0.8647	High Similarity	NPC472914
0.8647	High Similarity	NPC472911
0.8647	High Similarity	NPC203891
0.8647	High Similarity	NPC110070
0.8644	High Similarity	NPC289244
0.8636	High Similarity	NPC118128
0.8636	High Similarity	NPC121333
0.8636	High Similarity	NPC28589
0.8636	High Similarity	NPC248593
0.8629	High Similarity	NPC242395
0.8629	High Similarity	NPC288813
0.8629	High Similarity	NPC177480
0.8629	High Similarity	NPC165456
0.8621	High Similarity	NPC173292
0.8621	High Similarity	NPC120593
0.8621	High Similarity	NPC272560
0.8621	High Similarity	NPC476056
0.8619	High Similarity	NPC226725
0.8613	High Similarity	NPC207690
0.8613	High Similarity	NPC12461
0.8613	High Similarity	NPC273959
0.8613	High Similarity	NPC476931
0.8613	High Similarity	NPC41301
0.8605	High Similarity	NPC278052
0.8605	High Similarity	NPC29876
0.8605	High Similarity	NPC472275
0.8605	High Similarity	NPC234644
0.8605	High Similarity	NPC40491
0.8605	High Similarity	NPC167678
0.8603	High Similarity	NPC244903
0.8603	High Similarity	NPC120102
0.8596	High Similarity	NPC288669
0.8596	High Similarity	NPC261004
0.8596	High Similarity	NPC204854
0.8596	High Similarity	NPC185258
0.8596	High Similarity	NPC9609
0.8596	High Similarity	NPC19687
0.8596	High Similarity	NPC197856
0.8596	High Similarity	NPC152166
0.8596	High Similarity	NPC22472
0.8596	High Similarity	NPC115798
0.8596	High Similarity	NPC143828
0.8596	High Similarity	NPC105242
0.8596	High Similarity	NPC18607
0.8596	High Similarity	NPC55738
0.8596	High Similarity	NPC7846
0.8596	High Similarity	NPC191459
0.8596	High Similarity	NPC18772
0.8596	High Similarity	NPC471841
0.8596	High Similarity	NPC176300
0.8596	High Similarity	NPC130894
0.8596	High Similarity	NPC172770
0.8596	High Similarity	NPC25495
0.8596	High Similarity	NPC300943
0.8596	High Similarity	NPC4481
0.8596	High Similarity	NPC253634
0.8588	High Similarity	NPC245546
0.8588	High Similarity	NPC43243
0.8588	High Similarity	NPC303255
0.8588	High Similarity	NPC142339
0.8588	High Similarity	NPC68093
0.8588	High Similarity	NPC49824
0.8588	High Similarity	NPC266960
0.8588	High Similarity	NPC292107
0.8588	High Similarity	NPC191146

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 NPC476170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	1002
0.2-0.3	1864
0.3-0.4	2818
0.4-0.5	1795
0.5-0.6	820
0.6-0.7	298
0.7-0.8	102
0.8-0.85	18
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8563	High Similarity	NPD6166	Phase 2
0.8563	High Similarity	NPD6167	Clinical (unspecified phase)
0.8563	High Similarity	NPD6168	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD3882	Suspended
0.8471	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD5494	Approved
0.8304	Intermediate Similarity	NPD1934	Approved
0.8182	Intermediate Similarity	NPD1247	Approved
0.8166	Intermediate Similarity	NPD1512	Approved
0.815	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8122	Intermediate Similarity	NPD6797	Phase 2
0.8114	Intermediate Similarity	NPD3749	Approved
0.8077	Intermediate Similarity	NPD7251	Discontinued
0.8066	Intermediate Similarity	NPD7074	Phase 3
0.8047	Intermediate Similarity	NPD1511	Approved
0.8046	Intermediate Similarity	NPD1465	Phase 2
0.8033	Intermediate Similarity	NPD7808	Phase 3
0.8011	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7989	Intermediate Similarity	NPD3926	Phase 2
0.7967	Intermediate Similarity	NPD7472	Approved
0.7956	Intermediate Similarity	NPD3818	Discontinued
0.7933	Intermediate Similarity	NPD6232	Discontinued
0.7912	Intermediate Similarity	NPD5844	Phase 1
0.7877	Intermediate Similarity	NPD6959	Discontinued
0.7853	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD3751	Discontinued
0.7717	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7075	Discontinued
0.7672	Intermediate Similarity	NPD8434	Phase 2
0.767	Intermediate Similarity	NPD6599	Discontinued
0.7667	Intermediate Similarity	NPD919	Approved
0.764	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD3787	Discontinued
0.7602	Intermediate Similarity	NPD2800	Approved
0.7598	Intermediate Similarity	NPD5402	Approved
0.7596	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6559	Discontinued
0.7592	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4380	Phase 2
0.7554	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7819	Suspended
0.7529	Intermediate Similarity	NPD6799	Approved
0.7528	Intermediate Similarity	NPD7411	Suspended
0.7526	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3750	Approved
0.7442	Intermediate Similarity	NPD1549	Phase 2
0.7427	Intermediate Similarity	NPD6099	Approved
0.7427	Intermediate Similarity	NPD6100	Approved
0.7391	Intermediate Similarity	NPD7199	Phase 2
0.7389	Intermediate Similarity	NPD6801	Discontinued
0.738	Intermediate Similarity	NPD7228	Approved
0.7368	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD2403	Approved
0.7341	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD943	Approved
0.7333	Intermediate Similarity	NPD7907	Approved
0.7321	Intermediate Similarity	NPD4111	Phase 1
0.7321	Intermediate Similarity	NPD4665	Approved
0.7314	Intermediate Similarity	NPD2309	Approved
0.7288	Intermediate Similarity	NPD2534	Approved
0.7288	Intermediate Similarity	NPD2532	Approved
0.7288	Intermediate Similarity	NPD2533	Approved
0.7283	Intermediate Similarity	NPD1471	Phase 3
0.7283	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.725	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1240	Approved
0.7232	Intermediate Similarity	NPD7390	Discontinued
0.7231	Intermediate Similarity	NPD4287	Approved
0.7225	Intermediate Similarity	NPD2796	Approved
0.7222	Intermediate Similarity	NPD3226	Approved
0.7216	Intermediate Similarity	NPD8150	Discontinued
0.7207	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5403	Approved
0.7202	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7768	Phase 2
0.7168	Intermediate Similarity	NPD3748	Approved
0.7164	Intermediate Similarity	NPD6777	Approved
0.7164	Intermediate Similarity	NPD6780	Approved
0.7164	Intermediate Similarity	NPD6782	Approved
0.7164	Intermediate Similarity	NPD6776	Approved
0.7164	Intermediate Similarity	NPD6779	Approved
0.7164	Intermediate Similarity	NPD6778	Approved
0.7164	Intermediate Similarity	NPD6781	Approved
0.7159	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1607	Approved
0.715	Intermediate Similarity	NPD8312	Approved
0.715	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7129	Intermediate Similarity	NPD2493	Approved
0.7129	Intermediate Similarity	NPD2494	Approved
0.7111	Intermediate Similarity	NPD920	Approved
0.7108	Intermediate Similarity	NPD4583	Approved
0.7108	Intermediate Similarity	NPD4582	Approved
0.7104	Intermediate Similarity	NPD37	Approved
0.7103	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1243	Approved
0.7097	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5401	Approved
0.7081	Intermediate Similarity	NPD4967	Phase 2
0.7081	Intermediate Similarity	NPD4965	Approved
0.7081	Intermediate Similarity	NPD4966	Approved
0.7067	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD4002	Approved
0.7059	Intermediate Similarity	NPD7696	Phase 3
0.7059	Intermediate Similarity	NPD7697	Approved
0.7059	Intermediate Similarity	NPD4004	Approved
0.7059	Intermediate Similarity	NPD7698	Approved
0.7044	Intermediate Similarity	NPD3452	Approved
0.7044	Intermediate Similarity	NPD3450	Approved
0.7039	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1613	Approved
0.7035	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2935	Discontinued
0.7024	Intermediate Similarity	NPD7871	Phase 2
0.7024	Intermediate Similarity	NPD7870	Phase 2
0.7022	Intermediate Similarity	NPD6190	Approved
0.701	Intermediate Similarity	NPD3057	Approved
0.7006	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7701	Phase 2
0.7	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD447	Suspended
0.6989	Remote Similarity	NPD2346	Discontinued
0.6984	Remote Similarity	NPD7229	Phase 3
0.6971	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8151	Discontinued
0.6966	Remote Similarity	NPD4628	Phase 3
0.6959	Remote Similarity	NPD7685	Pre-registration
0.6959	Remote Similarity	NPD7240	Approved
0.6954	Remote Similarity	NPD6651	Approved
0.6938	Remote Similarity	NPD7874	Approved
0.6938	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2490	Approved
0.6935	Remote Similarity	NPD2488	Approved
0.6931	Remote Similarity	NPD2975	Approved
0.6931	Remote Similarity	NPD2974	Approved
0.6931	Remote Similarity	NPD2973	Approved
0.6927	Remote Similarity	NPD3533	Approved
0.6927	Remote Similarity	NPD2972	Approved
0.6927	Remote Similarity	NPD2491	Approved
0.6927	Remote Similarity	NPD2163	Approved
0.6923	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6534	Approved
0.6915	Remote Similarity	NPD6535	Approved
0.6912	Remote Similarity	NPD4580	Approved
0.6905	Remote Similarity	NPD7801	Approved
0.6905	Remote Similarity	NPD5676	Approved
0.6901	Remote Similarity	NPD4908	Phase 1
0.6897	Remote Similarity	NPD7699	Phase 2
0.6897	Remote Similarity	NPD7700	Phase 2
0.6897	Remote Similarity	NPD230	Phase 1
0.6895	Remote Similarity	NPD5711	Approved
0.6895	Remote Similarity	NPD5710	Approved
0.6889	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3300	Phase 2
0.6888	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5761	Phase 2
0.6882	Remote Similarity	NPD5760	Phase 2
0.6875	Remote Similarity	NPD2799	Discontinued
0.686	Remote Similarity	NPD4625	Phase 3
0.686	Remote Similarity	NPD3027	Phase 3
0.6845	Remote Similarity	NPD3448	Approved
0.6845	Remote Similarity	NPD2296	Approved
0.6837	Remote Similarity	NPD7549	Discontinued
0.683	Remote Similarity	NPD7048	Phase 3
0.6821	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3268	Approved
0.6821	Remote Similarity	NPD3764	Approved
0.6812	Remote Similarity	NPD7680	Approved
0.6793	Remote Similarity	NPD1653	Approved
0.6786	Remote Similarity	NPD6764	Approved
0.6786	Remote Similarity	NPD6765	Approved
0.6779	Remote Similarity	NPD8319	Approved
0.6779	Remote Similarity	NPD8320	Phase 1
0.6778	Remote Similarity	NPD7003	Approved
0.6765	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7095	Approved
0.6763	Remote Similarity	NPD6823	Phase 2
0.6757	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4107	Approved
0.6743	Remote Similarity	NPD4060	Phase 1
0.6742	Remote Similarity	NPD1551	Phase 2
0.6724	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7028	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