NPASS Compound

Structure

CID187398 OpenBabel06191715562D 28 31 0 0 1 0 0 0 0 0999 V2000 -5.1962 1.0000 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -0.8660 -1.5000 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 -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 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 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 -1.7321 0.0000 0.0000 C 0 0 2 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 0.0000 1.0000 0.0000 C 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 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 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 0.0000 -0.0000 0.0000 O 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 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 16 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 14 2 0 0 0 0 9 21 1 0 0 0 0 10 19 2 0 0 0 0 12 20 2 0 0 0 0 12 26 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 9 1 6 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 22 2 0 0 0 0 16 28 1 0 0 0 0 17 23 1 0 0 0 0 18 11 1 1 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.1
Volume:	369.48
LogP:	1.66
LogD:	1.718
LogS:	-4.149
# Rotatable Bonds:	4
TPSA:	107.59
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.658
Synthetic Accessibility Score:	3.447
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.248
MDCK Permeability:	2.6557994715403765e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.514
Plasma Protein Binding (PPB):	77.67658996582031%
Volume Distribution (VD):	0.733
Pgp-substrate:	19.542110443115234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.206
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.342
CYP2C9-inhibitor:	0.533
CYP2C9-substrate:	0.684
CYP2D6-inhibitor:	0.26
CYP2D6-substrate:	0.669
CYP3A4-inhibitor:	0.666
CYP3A4-substrate:	0.737

ADMET: Excretion

Clearance (CL):	6.0
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.229
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.219
Skin Sensitization:	0.295
Carcinogencity:	0.827
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC187398

Natural Product ID:	NPC187398
*Common Name:**	Daphneticin
IUPAC Name:	(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
Synonyms:	Daphneticin
Standard InCHIKey:	QLFQDIADUIVNRF-CRAIPNDOSA-N
Standard InCHI:	InChI=1S/C20H18O8/c1-24-13-7-11(8-14(25-2)17(13)23)18-15(9-21)27-20-12(26-18)5-3-10-4-6-16(22)28-19(10)20/h3-8,15,18,21,23H,9H2,1-2H3/t15-,18-/m1/s1
SMILES:	OC[C@H]1Oc2c(O[C@@H]1c1cc(OC)c(c(c1)OC)O)ccc1c2oc(=O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL584162
PubChem CID:	158341
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0002545] Coumarinolignans

*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
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32997496]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26557	Daphne tangutica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26557	Daphne tangutica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26557	Daphne tangutica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4035	Daphne odora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12814	Daphne retusa	Species	Thymelaeaceae	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	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	300000.0	nM	PMID[572606]
NPT1592	Individual Protein	Dipeptidyl peptidase IV	Homo sapiens	IC50	=	14130.0	nM	PMID[572607]

☑ 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 NPC187398 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	392
0.1-0.2	1731
0.2-0.3	4633
0.3-0.4	9746
0.4-0.5	8082
0.5-0.6	3934
0.6-0.7	5195
0.7-0.8	4915
0.8-0.85	2324
0.85-0.9	1514
0.9-0.95	218
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476348
0.9929	High Similarity	NPC476347
0.9859	High Similarity	NPC205727
0.9859	High Similarity	NPC21184
0.9859	High Similarity	NPC294522
0.9859	High Similarity	NPC120426
0.9789	High Similarity	NPC176903
0.9789	High Similarity	NPC30688
0.9648	High Similarity	NPC15577
0.9586	High Similarity	NPC163598
0.9586	High Similarity	NPC120774
0.9586	High Similarity	NPC264875
0.9521	High Similarity	NPC150442
0.9452	High Similarity	NPC169404
0.9452	High Similarity	NPC176186
0.9452	High Similarity	NPC53587
0.9441	High Similarity	NPC268515
0.9441	High Similarity	NPC40222
0.932	High Similarity	NPC476352
0.932	High Similarity	NPC215060
0.931	High Similarity	NPC93924
0.9296	High Similarity	NPC193722
0.9296	High Similarity	NPC278469
0.9286	High Similarity	NPC126206
0.9252	High Similarity	NPC213197
0.9247	High Similarity	NPC475250
0.9247	High Similarity	NPC106138
0.9241	High Similarity	NPC41844
0.9231	High Similarity	NPC34245
0.9231	High Similarity	NPC91492
0.9231	High Similarity	NPC7439
0.9231	High Similarity	NPC256555
0.9231	High Similarity	NPC110067
0.9225	High Similarity	NPC224876
0.9225	High Similarity	NPC83375
0.9214	High Similarity	NPC471665
0.9214	High Similarity	NPC471664
0.9195	High Similarity	NPC8712
0.9172	High Similarity	NPC199928
0.9167	High Similarity	NPC471763
0.9155	High Similarity	NPC267291
0.9149	High Similarity	NPC474886
0.9116	High Similarity	NPC313334
0.9116	High Similarity	NPC206264
0.9116	High Similarity	NPC212670
0.911	High Similarity	NPC231149
0.911	High Similarity	NPC52740
0.9091	High Similarity	NPC300611
0.9085	High Similarity	NPC13067
0.9085	High Similarity	NPC164148
0.9085	High Similarity	NPC43500
0.9078	High Similarity	NPC471719
0.9078	High Similarity	NPC16435
0.9078	High Similarity	NPC306441
0.9071	High Similarity	NPC92830
0.9071	High Similarity	NPC135127
0.9071	High Similarity	NPC111635
0.9071	High Similarity	NPC170694
0.9067	High Similarity	NPC268484
0.9054	High Similarity	NPC114740
0.9048	High Similarity	NPC48366
0.9048	High Similarity	NPC139839
0.9048	High Similarity	NPC96294
0.9048	High Similarity	NPC478237
0.9041	High Similarity	NPC205361
0.9034	High Similarity	NPC232228
0.9034	High Similarity	NPC292443
0.9014	High Similarity	NPC76336
0.9014	High Similarity	NPC211549
0.9014	High Similarity	NPC20511
0.9014	High Similarity	NPC95162
0.9014	High Similarity	NPC139548
0.9014	High Similarity	NPC148835
0.9014	High Similarity	NPC52086
0.9007	High Similarity	NPC61946
0.9007	High Similarity	NPC474206
0.9007	High Similarity	NPC470356
0.9007	High Similarity	NPC94750
0.9007	High Similarity	NPC121812
0.9007	High Similarity	NPC260898
0.9007	High Similarity	NPC224941
0.9007	High Similarity	NPC112246
0.9007	High Similarity	NPC311430
0.9007	High Similarity	NPC112939
0.9007	High Similarity	NPC234333
0.9007	High Similarity	NPC47398
0.9	High Similarity	NPC229442
0.9	High Similarity	NPC149735
0.9	High Similarity	NPC223720
0.9	High Similarity	NPC168059
0.898	High Similarity	NPC178129
0.8973	High Similarity	NPC473909
0.8973	High Similarity	NPC143120
0.8973	High Similarity	NPC226722
0.8973	High Similarity	NPC274960
0.8966	High Similarity	NPC138212
0.8966	High Similarity	NPC478239
0.8947	High Similarity	NPC284810
0.8944	High Similarity	NPC82271
0.8944	High Similarity	NPC269091
0.8944	High Similarity	NPC474639
0.8944	High Similarity	NPC230734
0.8944	High Similarity	NPC126682
0.8944	High Similarity	NPC227503
0.8944	High Similarity	NPC302701
0.8936	High Similarity	NPC309744
0.8929	High Similarity	NPC245120
0.8929	High Similarity	NPC184447
0.8929	High Similarity	NPC35932
0.8929	High Similarity	NPC5423
0.8929	High Similarity	NPC160991
0.8929	High Similarity	NPC16208
0.8929	High Similarity	NPC7903
0.8912	High Similarity	NPC125755
0.891	High Similarity	NPC142614
0.8904	High Similarity	NPC185127
0.8904	High Similarity	NPC471824
0.8897	High Similarity	NPC475084
0.8897	High Similarity	NPC140502
0.8897	High Similarity	NPC157816
0.8896	High Similarity	NPC53889
0.8896	High Similarity	NPC24164
0.8889	High Similarity	NPC125495
0.8881	High Similarity	NPC38874
0.8881	High Similarity	NPC176051
0.8881	High Similarity	NPC103976
0.8881	High Similarity	NPC326797
0.8881	High Similarity	NPC102904
0.8881	High Similarity	NPC107551
0.8881	High Similarity	NPC474282
0.8874	High Similarity	NPC474656
0.8873	High Similarity	NPC472337
0.8873	High Similarity	NPC164787
0.8873	High Similarity	NPC214729
0.8873	High Similarity	NPC151224
0.8865	High Similarity	NPC475840
0.8865	High Similarity	NPC263064
0.8865	High Similarity	NPC11060
0.8857	High Similarity	NPC73738
0.8857	High Similarity	NPC472597
0.8844	High Similarity	NPC161700
0.8844	High Similarity	NPC252292
0.8844	High Similarity	NPC34587
0.8844	High Similarity	NPC34927
0.8844	High Similarity	NPC277867
0.8844	High Similarity	NPC469701
0.8844	High Similarity	NPC476382
0.8844	High Similarity	NPC100998
0.8844	High Similarity	NPC475096
0.8844	High Similarity	NPC163898
0.8831	High Similarity	NPC87317
0.8828	High Similarity	NPC195357
0.8828	High Similarity	NPC186406
0.8828	High Similarity	NPC178054
0.8828	High Similarity	NPC152771
0.8828	High Similarity	NPC471389
0.8819	High Similarity	NPC279573
0.8811	High Similarity	NPC162659
0.8811	High Similarity	NPC286843
0.8811	High Similarity	NPC26954
0.8811	High Similarity	NPC248727
0.8811	High Similarity	NPC470802
0.8811	High Similarity	NPC270456
0.8811	High Similarity	NPC265433
0.8811	High Similarity	NPC38099
0.8811	High Similarity	NPC472334
0.8811	High Similarity	NPC472336
0.8808	High Similarity	NPC470264
0.8808	High Similarity	NPC75695
0.8803	High Similarity	NPC310854
0.8803	High Similarity	NPC119060
0.8803	High Similarity	NPC476387
0.8803	High Similarity	NPC474600
0.8803	High Similarity	NPC317380
0.8803	High Similarity	NPC309953
0.8803	High Similarity	NPC237594
0.8803	High Similarity	NPC249791
0.88	High Similarity	NPC477381
0.8794	High Similarity	NPC201587
0.8794	High Similarity	NPC15658
0.8794	High Similarity	NPC202762
0.8794	High Similarity	NPC86655
0.8794	High Similarity	NPC253105
0.8794	High Similarity	NPC61477
0.8794	High Similarity	NPC78770
0.8794	High Similarity	NPC126029
0.8794	High Similarity	NPC127624
0.8794	High Similarity	NPC219876
0.8794	High Similarity	NPC261619
0.8794	High Similarity	NPC185604
0.8792	High Similarity	NPC473408
0.8792	High Similarity	NPC102934
0.8792	High Similarity	NPC252402
0.8786	High Similarity	NPC19242
0.8786	High Similarity	NPC91291
0.8786	High Similarity	NPC476399
0.8786	High Similarity	NPC472338
0.8784	High Similarity	NPC287275
0.8784	High Similarity	NPC476865
0.8784	High Similarity	NPC99515

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 NPC187398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	933
0.2-0.3	1996
0.3-0.4	2569
0.4-0.5	1788
0.5-0.6	949
0.6-0.7	379
0.7-0.8	106
0.8-0.85	34
0.85-0.9	23
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9116	High Similarity	NPD1653	Approved
0.8794	High Similarity	NPD1612	Clinical (unspecified phase)
0.8794	High Similarity	NPD1613	Approved
0.8701	High Similarity	NPD4868	Clinical (unspecified phase)
0.8582	High Similarity	NPD3027	Phase 3
0.8511	High Similarity	NPD1529	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD7266	Discontinued
0.8395	Intermediate Similarity	NPD7054	Approved
0.8387	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD7472	Approved
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8322	Intermediate Similarity	NPD1652	Phase 2
0.8303	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD5844	Phase 1
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8221	Intermediate Similarity	NPD3818	Discontinued
0.8219	Intermediate Similarity	NPD5124	Phase 1
0.8219	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1465	Phase 2
0.8217	Intermediate Similarity	NPD2801	Approved
0.8217	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8143	Intermediate Similarity	NPD422	Phase 1
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8084	Intermediate Similarity	NPD7808	Phase 3
0.8063	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5402	Approved
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD4908	Phase 1
0.8	Intermediate Similarity	NPD3882	Suspended
0.7987	Intermediate Similarity	NPD1511	Approved
0.7976	Intermediate Similarity	NPD7549	Discontinued
0.795	Intermediate Similarity	NPD7075	Discontinued
0.7949	Intermediate Similarity	NPD5403	Approved
0.7901	Intermediate Similarity	NPD6234	Discontinued
0.7892	Intermediate Similarity	NPD7228	Approved
0.7891	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1512	Approved
0.7857	Intermediate Similarity	NPD1548	Phase 1
0.7857	Intermediate Similarity	NPD6190	Approved
0.7821	Intermediate Similarity	NPD5401	Approved
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.7812	Intermediate Similarity	NPD37	Approved
0.7805	Intermediate Similarity	NPD7199	Phase 2
0.7792	Intermediate Similarity	NPD3750	Approved
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4965	Approved
0.777	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1610	Phase 2
0.7706	Intermediate Similarity	NPD6559	Discontinued
0.7687	Intermediate Similarity	NPD3018	Phase 2
0.7667	Intermediate Similarity	NPD4060	Phase 1
0.7654	Intermediate Similarity	NPD7819	Suspended
0.7651	Intermediate Similarity	NPD6232	Discontinued
0.7643	Intermediate Similarity	NPD6799	Approved
0.764	Intermediate Similarity	NPD7411	Suspended
0.7636	Intermediate Similarity	NPD5494	Approved
0.7633	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD230	Phase 1
0.7605	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3225	Approved
0.7602	Intermediate Similarity	NPD7685	Pre-registration
0.759	Intermediate Similarity	NPD8127	Discontinued
0.7568	Intermediate Similarity	NPD2861	Phase 2
0.7564	Intermediate Similarity	NPD4628	Phase 3
0.7564	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1549	Phase 2
0.7547	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2982	Phase 2
0.7534	Intermediate Similarity	NPD2983	Phase 2
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1091	Approved
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4340	Discontinued
0.7484	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3748	Approved
0.7467	Intermediate Similarity	NPD4625	Phase 3
0.7466	Intermediate Similarity	NPD2981	Phase 2
0.7455	Intermediate Similarity	NPD7768	Phase 2
0.7448	Intermediate Similarity	NPD3496	Discontinued
0.7432	Intermediate Similarity	NPD2797	Approved
0.7421	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1551	Phase 2
0.7419	Intermediate Similarity	NPD2796	Approved
0.7417	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6798	Discontinued
0.7415	Intermediate Similarity	NPD4749	Approved
0.7399	Intermediate Similarity	NPD7240	Approved
0.7394	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3751	Discontinued
0.7368	Intermediate Similarity	NPD6233	Phase 2
0.7365	Intermediate Similarity	NPD919	Approved
0.7362	Intermediate Similarity	NPD6599	Discontinued
0.7357	Intermediate Similarity	NPD228	Approved
0.7355	Intermediate Similarity	NPD7033	Discontinued
0.7355	Intermediate Similarity	NPD1510	Phase 2
0.7353	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3687	Approved
0.7346	Intermediate Similarity	NPD3686	Approved
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7325	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7212	Phase 2
0.7312	Intermediate Similarity	NPD4357	Discontinued
0.7312	Intermediate Similarity	NPD7213	Phase 3
0.7308	Intermediate Similarity	NPD2935	Discontinued
0.7303	Intermediate Similarity	NPD3268	Approved
0.7303	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5536	Phase 2
0.729	Intermediate Similarity	NPD7097	Phase 1
0.7285	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6959	Discontinued
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD1933	Approved
0.7267	Intermediate Similarity	NPD7447	Phase 1
0.7261	Intermediate Similarity	NPD5763	Approved
0.7261	Intermediate Similarity	NPD5762	Approved
0.7237	Intermediate Similarity	NPD7095	Approved
0.7235	Intermediate Similarity	NPD3787	Discontinued
0.7233	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2424	Discontinued
0.7208	Intermediate Similarity	NPD1558	Phase 1
0.7202	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3749	Approved
0.72	Intermediate Similarity	NPD7039	Approved
0.72	Intermediate Similarity	NPD7038	Approved
0.7195	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5535	Approved
0.7179	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4538	Approved
0.7179	Intermediate Similarity	NPD4536	Approved
0.7171	Intermediate Similarity	NPD6832	Phase 2
0.7152	Intermediate Similarity	NPD3540	Phase 1
0.7152	Intermediate Similarity	NPD4678	Approved
0.7152	Intermediate Similarity	NPD4675	Approved
0.7151	Intermediate Similarity	NPD6843	Phase 3
0.7151	Intermediate Similarity	NPD6842	Approved
0.7151	Intermediate Similarity	NPD6841	Approved
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7125	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4110	Phase 3
0.7119	Intermediate Similarity	NPD8313	Approved
0.7119	Intermediate Similarity	NPD8312	Approved
0.7115	Intermediate Similarity	NPD6653	Approved
0.7097	Intermediate Similarity	NPD4140	Approved
0.7097	Intermediate Similarity	NPD1240	Approved
0.7097	Intermediate Similarity	NPD3620	Phase 2
0.7097	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD3539	Phase 1
0.7089	Intermediate Similarity	NPD6099	Approved
0.7089	Intermediate Similarity	NPD6032	Approved
0.7086	Intermediate Similarity	NPD1203	Approved
0.7083	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5353	Approved
0.7081	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1296	Phase 2
0.7071	Intermediate Similarity	NPD290	Approved
0.7071	Intermediate Similarity	NPD1358	Approved
0.7063	Intermediate Similarity	NPD7843	Approved
0.7063	Intermediate Similarity	NPD5177	Phase 3
0.7051	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3705	Approved
0.7044	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5058	Phase 3
0.7034	Intermediate Similarity	NPD6671	Approved
0.7034	Intermediate Similarity	NPD7157	Approved
0.7033	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4062	Phase 3
0.7027	Intermediate Similarity	NPD4626	Approved
0.7027	Intermediate Similarity	NPD1778	Approved
0.7025	Intermediate Similarity	NPD5960	Phase 3
0.7025	Intermediate Similarity	NPD5588	Approved
0.7021	Intermediate Similarity	NPD7680	Approved
0.7021	Intermediate Similarity	NPD2684	Approved
0.702	Intermediate Similarity	NPD8651	Approved
0.7019	Intermediate Similarity	NPD8166	Discontinued
0.7018	Intermediate Similarity	NPD5677	Discontinued
0.7012	Intermediate Similarity	NPD6273	Approved
0.7006	Intermediate Similarity	NPD1607	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