NPASS Compound

Structure

CID269495 OpenBabel06191716072D 26 28 0 0 1 0 0 0 0 0999 V2000 -1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 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 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 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 -1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -6.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 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 -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 -1.7321 -6.0000 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 -3.5491 -0.1910 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 5 2 0 0 0 0 4 16 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 17 1 0 0 0 0 8 25 1 0 0 0 0 9 24 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 23 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	4.425
LogD:	3.814
LogS:	-3.807
# Rotatable Bonds:	6
TPSA:	72.81
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	3.509
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.819
MDCK Permeability:	1.8002128854277544e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.838
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	89.15682220458984%
Volume Distribution (VD):	0.468
Pgp-substrate:	9.514534950256348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.13
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.633
CYP2D6-substrate:	0.789
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	11.081
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.434
Drug-inuced Liver Injury (DILI):	0.351
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.497
Skin Sensitization:	0.147
Carcinogencity:	0.155
Eye Corrosion:	0.003
Eye Irritation:	0.109
Respiratory Toxicity:	0.423

Download Data

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

Natural Product: NPC269495

Natural Product ID:	NPC269495
*Common Name:**	Notopterol
IUPAC Name:	4-[(2E)-5-hydroxy-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
Synonyms:	notopterol
Standard InCHIKey:	BKIACVAZUKISOR-MKMNVTDBSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-13(2)10-15(22)11-14(3)6-8-25-21-16-4-5-20(23)26-19(16)12-18-17(21)7-9-24-18/h4-7,9-10,12,15,22H,8,11H2,1-3H3/b14-6+
SMILES:	C/C(=CCOc1c2ccoc2cc2c1ccc(=O)o2)/CC(C=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL258939
PubChem CID:	5320227
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO30526	0topterygium incisum	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[20707067]
NPO30526	0topterygium incisum	n.a.	n.a.	n.a.	n.a.	rhizome	n.a.	PMID[20707067]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO30526	0topterygium incisum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO14148.1	Panax pseudo - ginseng var. notoginseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO14105.2	Panax pseudo-ginseng var. notoginseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14105.2	Panax pseudo-ginseng var. notoginseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30526	0topterygium incisum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	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
Ki	4
Others	1

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1069	Individual Protein	Mu opioid receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[566446]
NPT1167	Individual Protein	Delta opioid receptor	Mus musculus	Ki	>	10000.0	nM	PMID[566446]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[566446]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	Ki	=	1422.0	nM	PMID[566446]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	Activity	>	50.0	%	PMID[566446]

☑ 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 NPC269495 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	346
0.1-0.2	1548
0.2-0.3	3725
0.3-0.4	9042
0.4-0.5	10048
0.5-0.6	4107
0.6-0.7	5877
0.7-0.8	5401
0.8-0.85	1808
0.85-0.9	664
0.9-0.95	125
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC49009
0.9737	High Similarity	NPC169
0.9673	High Similarity	NPC14822
0.9608	High Similarity	NPC303210
0.9608	High Similarity	NPC239270
0.9608	High Similarity	NPC95472
0.9597	High Similarity	NPC191104
0.953	High Similarity	NPC88445
0.9477	High Similarity	NPC270044
0.9467	High Similarity	NPC155882
0.9396	High Similarity	NPC74539
0.9396	High Similarity	NPC304443
0.929	High Similarity	NPC476349
0.929	High Similarity	NPC476350
0.9262	High Similarity	NPC246903
0.9221	High Similarity	NPC250769
0.9221	High Similarity	NPC295608
0.9221	High Similarity	NPC278010
0.9216	High Similarity	NPC263676
0.9205	High Similarity	NPC266743
0.9161	High Similarity	NPC160015
0.9161	High Similarity	NPC247677
0.9156	High Similarity	NPC122365
0.9156	High Similarity	NPC131725
0.915	High Similarity	NPC290671
0.9145	High Similarity	NPC317492
0.9145	High Similarity	NPC226644
0.9145	High Similarity	NPC37226
0.9145	High Similarity	NPC39929
0.9145	High Similarity	NPC296030
0.9141	High Similarity	NPC107244
0.9133	High Similarity	NPC208584
0.9128	High Similarity	NPC166858
0.9128	High Similarity	NPC51146
0.9128	High Similarity	NPC313036
0.9108	High Similarity	NPC260296
0.9108	High Similarity	NPC115432
0.9103	High Similarity	NPC296957
0.9103	High Similarity	NPC260902
0.9085	High Similarity	NPC474735
0.9079	High Similarity	NPC168085
0.9073	High Similarity	NPC190572
0.9045	High Similarity	NPC244750
0.9032	High Similarity	NPC213608
0.9032	High Similarity	NPC1477
0.9026	High Similarity	NPC116604
0.9026	High Similarity	NPC170169
0.9024	High Similarity	NPC325176
0.9013	High Similarity	NPC130581
0.9013	High Similarity	NPC12148
0.9012	High Similarity	NPC51404
0.9	High Similarity	NPC294432
0.9	High Similarity	NPC136641
0.8993	High Similarity	NPC470856
0.8981	High Similarity	NPC65504
0.8974	High Similarity	NPC474542
0.8974	High Similarity	NPC198490
0.8974	High Similarity	NPC108937
0.8974	High Similarity	NPC279218
0.8968	High Similarity	NPC5871
0.8968	High Similarity	NPC67654
0.8963	High Similarity	NPC224165
0.8961	High Similarity	NPC135303
0.8961	High Similarity	NPC78335
0.8961	High Similarity	NPC230713
0.8961	High Similarity	NPC148423
0.8957	High Similarity	NPC472584
0.8954	High Similarity	NPC135325
0.8947	High Similarity	NPC210826
0.8947	High Similarity	NPC51641
0.8947	High Similarity	NPC300267
0.8944	High Similarity	NPC323137
0.894	High Similarity	NPC474939
0.894	High Similarity	NPC33653
0.894	High Similarity	NPC470909
0.894	High Similarity	NPC184738
0.894	High Similarity	NPC96216
0.8938	High Similarity	NPC155640
0.8933	High Similarity	NPC254010
0.8926	High Similarity	NPC262635
0.8924	High Similarity	NPC40583
0.8917	High Similarity	NPC475797
0.8917	High Similarity	NPC129053
0.8917	High Similarity	NPC109967
0.8917	High Similarity	NPC78554
0.8917	High Similarity	NPC321372
0.8917	High Similarity	NPC469936
0.8917	High Similarity	NPC474609
0.8917	High Similarity	NPC474738
0.891	High Similarity	NPC183874
0.891	High Similarity	NPC472462
0.8903	High Similarity	NPC474744
0.8903	High Similarity	NPC156244
0.8903	High Similarity	NPC472423
0.8903	High Similarity	NPC474772
0.8902	High Similarity	NPC233956
0.8896	High Similarity	NPC37208
0.8896	High Similarity	NPC221868
0.8896	High Similarity	NPC120220
0.8896	High Similarity	NPC178202
0.8889	High Similarity	NPC198427
0.8889	High Similarity	NPC320789
0.8889	High Similarity	NPC285748
0.8882	High Similarity	NPC259007
0.8882	High Similarity	NPC133060
0.8882	High Similarity	NPC224714
0.8882	High Similarity	NPC87486
0.8882	High Similarity	NPC124780
0.8882	High Similarity	NPC204088
0.8882	High Similarity	NPC329215
0.8882	High Similarity	NPC470554
0.8882	High Similarity	NPC288910
0.8882	High Similarity	NPC118059
0.8875	High Similarity	NPC193998
0.8874	High Similarity	NPC472344
0.8874	High Similarity	NPC112829
0.8874	High Similarity	NPC470556
0.8854	High Similarity	NPC148938
0.8848	High Similarity	NPC53917
0.8846	High Similarity	NPC327269
0.8846	High Similarity	NPC285623
0.8846	High Similarity	NPC256141
0.8846	High Similarity	NPC253872
0.8846	High Similarity	NPC130015
0.8846	High Similarity	NPC31627
0.8846	High Similarity	NPC38361
0.8846	High Similarity	NPC476238
0.8839	High Similarity	NPC321896
0.8839	High Similarity	NPC470908
0.8839	High Similarity	NPC180351
0.8839	High Similarity	NPC476185
0.8839	High Similarity	NPC61258
0.8839	High Similarity	NPC472406
0.8839	High Similarity	NPC472421
0.8831	High Similarity	NPC306788
0.8831	High Similarity	NPC272194
0.8827	High Similarity	NPC155264
0.8827	High Similarity	NPC210460
0.8827	High Similarity	NPC193881
0.8827	High Similarity	NPC67450
0.8824	High Similarity	NPC470910
0.8824	High Similarity	NPC472629
0.8824	High Similarity	NPC470322
0.8824	High Similarity	NPC154217
0.8816	High Similarity	NPC470553
0.8816	High Similarity	NPC476178
0.8816	High Similarity	NPC307895
0.8816	High Similarity	NPC51887
0.8816	High Similarity	NPC302181
0.8816	High Similarity	NPC225884
0.8816	High Similarity	NPC117836
0.8816	High Similarity	NPC475705
0.8812	High Similarity	NPC45124
0.8812	High Similarity	NPC216092
0.8812	High Similarity	NPC30655
0.8812	High Similarity	NPC74854
0.8808	High Similarity	NPC321980
0.8808	High Similarity	NPC470087
0.88	High Similarity	NPC137009
0.88	High Similarity	NPC139554
0.88	High Similarity	NPC37206
0.88	High Similarity	NPC472515
0.8792	High Similarity	NPC253616
0.879	High Similarity	NPC41719
0.879	High Similarity	NPC235333
0.8782	High Similarity	NPC318424
0.8782	High Similarity	NPC472407
0.8782	High Similarity	NPC471675
0.878	High Similarity	NPC281835
0.8774	High Similarity	NPC19238
0.8774	High Similarity	NPC5173
0.8766	High Similarity	NPC17816
0.8766	High Similarity	NPC202494
0.8758	High Similarity	NPC311741
0.8758	High Similarity	NPC219861
0.8758	High Similarity	NPC234629
0.8758	High Similarity	NPC297788
0.8758	High Similarity	NPC470890
0.8758	High Similarity	NPC230943
0.8758	High Similarity	NPC196137
0.8758	High Similarity	NPC469953
0.8758	High Similarity	NPC1886
0.875	High Similarity	NPC243509
0.875	High Similarity	NPC304839
0.875	High Similarity	NPC220582
0.875	High Similarity	NPC36181
0.875	High Similarity	NPC53192
0.8742	High Similarity	NPC164110
0.8742	High Similarity	NPC246647
0.8742	High Similarity	NPC96342
0.8742	High Similarity	NPC268360
0.8742	High Similarity	NPC212967
0.8734	High Similarity	NPC233776
0.8734	High Similarity	NPC297531
0.8734	High Similarity	NPC213936
0.8733	High Similarity	NPC36414
0.8726	High Similarity	NPC41326
0.8726	High Similarity	NPC473996
0.8726	High Similarity	NPC207624
0.8725	High Similarity	NPC268081

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 NPC269495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	920
0.2-0.3	1722
0.3-0.4	2563
0.4-0.5	2065
0.5-0.6	1063
0.6-0.7	344
0.7-0.8	107
0.8-0.85	36
0.85-0.9	10
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9396	High Similarity	NPD920	Approved
0.9262	High Similarity	NPD642	Clinical (unspecified phase)
0.9128	High Similarity	NPD643	Clinical (unspecified phase)
0.8926	High Similarity	NPD1243	Approved
0.8688	High Similarity	NPD919	Approved
0.8636	High Similarity	NPD4378	Clinical (unspecified phase)
0.8608	High Similarity	NPD6801	Discontinued
0.8563	High Similarity	NPD6559	Discontinued
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8544	High Similarity	NPD7411	Suspended
0.8509	High Similarity	NPD7075	Discontinued
0.8509	High Similarity	NPD3749	Approved
0.8481	Intermediate Similarity	NPD4380	Phase 2
0.8477	Intermediate Similarity	NPD2796	Approved
0.8438	Intermediate Similarity	NPD7819	Suspended
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD1247	Approved
0.8333	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8282	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD2534	Approved
0.828	Intermediate Similarity	NPD2532	Approved
0.828	Intermediate Similarity	NPD2533	Approved
0.8235	Intermediate Similarity	NPD1551	Phase 2
0.8221	Intermediate Similarity	NPD7768	Phase 2
0.8214	Intermediate Similarity	NPD3818	Discontinued
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1240	Approved
0.8141	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.811	Intermediate Similarity	NPD3882	Suspended
0.8072	Intermediate Similarity	NPD5494	Approved
0.8065	Intermediate Similarity	NPD2344	Approved
0.8063	Intermediate Similarity	NPD5403	Approved
0.8059	Intermediate Similarity	NPD5844	Phase 1
0.8059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2799	Discontinued
0.8049	Intermediate Similarity	NPD5402	Approved
0.8049	Intermediate Similarity	NPD3817	Phase 2
0.8039	Intermediate Similarity	NPD1607	Approved
0.8037	Intermediate Similarity	NPD1934	Approved
0.8025	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7988	Intermediate Similarity	NPD2801	Approved
0.7965	Intermediate Similarity	NPD5953	Discontinued
0.7953	Intermediate Similarity	NPD7286	Phase 2
0.7937	Intermediate Similarity	NPD5401	Approved
0.7917	Intermediate Similarity	NPD6959	Discontinued
0.7911	Intermediate Similarity	NPD4628	Phase 3
0.7892	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1511	Approved
0.787	Intermediate Similarity	NPD6232	Discontinued
0.7862	Intermediate Similarity	NPD2309	Approved
0.7853	Intermediate Similarity	NPD3226	Approved
0.7836	Intermediate Similarity	NPD7473	Discontinued
0.7821	Intermediate Similarity	NPD3748	Approved
0.7821	Intermediate Similarity	NPD7033	Discontinued
0.7797	Intermediate Similarity	NPD8434	Phase 2
0.7791	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6832	Phase 2
0.7746	Intermediate Similarity	NPD7054	Approved
0.7742	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5124	Phase 1
0.7719	Intermediate Similarity	NPD3926	Phase 2
0.7718	Intermediate Similarity	NPD9717	Approved
0.7701	Intermediate Similarity	NPD7472	Approved
0.7701	Intermediate Similarity	NPD7074	Phase 3
0.7682	Intermediate Similarity	NPD1203	Approved
0.7661	Intermediate Similarity	NPD5710	Approved
0.7661	Intermediate Similarity	NPD5711	Approved
0.7657	Intermediate Similarity	NPD6797	Phase 2
0.7614	Intermediate Similarity	NPD7251	Discontinued
0.761	Intermediate Similarity	NPD2346	Discontinued
0.758	Intermediate Similarity	NPD6651	Approved
0.7571	Intermediate Similarity	NPD7808	Phase 3
0.756	Intermediate Similarity	NPD5761	Phase 2
0.756	Intermediate Similarity	NPD5760	Phase 2
0.7558	Intermediate Similarity	NPD6808	Phase 2
0.7558	Intermediate Similarity	NPD7229	Phase 3
0.7557	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3268	Approved
0.7545	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD422	Phase 1
0.7516	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6005	Phase 3
0.75	Intermediate Similarity	NPD6002	Phase 3
0.75	Intermediate Similarity	NPD6004	Phase 3
0.75	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4308	Phase 3
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1465	Phase 2
0.7451	Intermediate Similarity	NPD2797	Approved
0.7425	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD230	Phase 1
0.7403	Intermediate Similarity	NPD1019	Discontinued
0.7401	Intermediate Similarity	NPD1729	Discontinued
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7337	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD411	Approved
0.7325	Intermediate Similarity	NPD1296	Phase 2
0.7312	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4361	Phase 2
0.731	Intermediate Similarity	NPD2296	Approved
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2654	Approved
0.7301	Intermediate Similarity	NPD1652	Phase 2
0.7294	Intermediate Similarity	NPD6279	Approved
0.7294	Intermediate Similarity	NPD6280	Approved
0.7294	Intermediate Similarity	NPD37	Approved
0.729	Intermediate Similarity	NPD2798	Approved
0.7284	Intermediate Similarity	NPD1471	Phase 3
0.7283	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3225	Approved
0.7267	Intermediate Similarity	NPD9545	Approved
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD6273	Approved
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7238	Intermediate Similarity	NPD8313	Approved
0.7238	Intermediate Similarity	NPD8312	Approved
0.7233	Intermediate Similarity	NPD943	Approved
0.7233	Intermediate Similarity	NPD4307	Phase 2
0.7228	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3267	Approved
0.7226	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7215	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3764	Approved
0.7209	Intermediate Similarity	NPD4288	Approved
0.72	Intermediate Similarity	NPD7199	Phase 2
0.7191	Intermediate Similarity	NPD3751	Discontinued
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD7003	Approved
0.7151	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7135	Intermediate Similarity	NPD5889	Approved
0.7135	Intermediate Similarity	NPD5890	Approved
0.7133	Intermediate Similarity	NPD9493	Approved
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1164	Approved
0.7113	Intermediate Similarity	NPD7584	Approved
0.7107	Intermediate Similarity	NPD6798	Discontinued
0.7093	Intermediate Similarity	NPD6844	Discontinued
0.7089	Intermediate Similarity	NPD4908	Phase 1
0.7086	Intermediate Similarity	NPD6234	Discontinued
0.7081	Intermediate Similarity	NPD1933	Approved
0.7079	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2403	Approved
0.7079	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3787	Discontinued
0.7059	Intermediate Similarity	NPD1653	Approved
0.7041	Intermediate Similarity	NPD8151	Discontinued
0.7039	Intermediate Similarity	NPD1548	Phase 1
0.7033	Intermediate Similarity	NPD6764	Approved
0.7033	Intermediate Similarity	NPD6765	Approved
0.7026	Intermediate Similarity	NPD7583	Approved
0.7022	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5405	Approved
0.7012	Intermediate Similarity	NPD5404	Approved
0.7012	Intermediate Similarity	NPD6099	Approved
0.7012	Intermediate Similarity	NPD5406	Approved
0.7012	Intermediate Similarity	NPD6100	Approved
0.7012	Intermediate Similarity	NPD5408	Approved
0.7012	Intermediate Similarity	NPD4476	Approved
0.7012	Intermediate Similarity	NPD4477	Approved
0.7006	Intermediate Similarity	NPD3887	Approved
0.7	Intermediate Similarity	NPD7177	Discontinued
0.699	Remote Similarity	NPD7585	Approved
0.6981	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6585	Discontinued
0.6973	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7782	Clinical (unspecified phase)

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