NPASS Compound

Structure

CID135127 OpenBabel06191715492D 29 30 0 0 1 0 0 0 0 0999 V2000 6.0622 4.5000 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 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 5.1962 -0.0000 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 0.8660 -0.5000 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 6.0622 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 7.7942 2.5000 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 2.5981 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 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 1.7321 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.6603 3.0000 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 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 29 1 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.15
Volume:	403.889
LogP:	2.426
LogD:	2.874
LogS:	-3.439
# Rotatable Bonds:	10
TPSA:	114.68
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	3.255
Fsp3:	0.286
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:	-4.898
MDCK Permeability:	1.403981150360778e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.338
Human Intestinal Absorption (HIA):	0.485
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.52
Plasma Protein Binding (PPB):	98.05398559570312%
Volume Distribution (VD):	0.42
Pgp-substrate:	3.7833046913146973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.795
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.574
CYP2C9-inhibitor:	0.244
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.166
CYP2D6-substrate:	0.837
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.565

ADMET: Excretion

Clearance (CL):	12.74
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.461
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.342
Skin Sensitization:	0.932
Carcinogencity:	0.207
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC135127

Natural Product ID:	NPC135127
*Common Name:**	Angeliferulate
IUPAC Name:	[2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-3-methoxypropyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:	Angeliferulate
Standard InCHIKey:	IYGJNXKQEYRFJG-WEVVVXLNSA-N
Standard InCHI:	InChI=1S/C21H24O8/c1-26-18-10-13(4-7-15(18)22)5-9-20(25)29-12-17(24)21(28-3)14-6-8-16(23)19(11-14)27-2/h4-11,17,21-24H,12H2,1-3H3/b9-5+
SMILES:	COC(c1ccc(c(c1)OC)O)C(COC(=O)/C=C/c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480460
PubChem CID:	11654315
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	31.0	%	PMID[543741]

☑ 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 NPC135127 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	291
0.1-0.2	1251
0.2-0.3	3629
0.3-0.4	8961
0.4-0.5	9509
0.5-0.6	3792
0.6-0.7	8106
0.7-0.8	5610
0.8-0.85	1107
0.85-0.9	372
0.9-0.95	65
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC126206
0.9542	High Similarity	NPC471665
0.9542	High Similarity	NPC471664
0.9478	High Similarity	NPC140502
0.9389	High Similarity	NPC476387
0.9389	High Similarity	NPC119060
0.9389	High Similarity	NPC237594
0.9389	High Similarity	NPC249791
0.937	High Similarity	NPC213552
0.937	High Similarity	NPC120225
0.9333	High Similarity	NPC67467
0.9302	High Similarity	NPC83062
0.9291	High Similarity	NPC289459
0.927	High Similarity	NPC34587
0.927	High Similarity	NPC252292
0.927	High Similarity	NPC473909
0.927	High Similarity	NPC34927
0.927	High Similarity	NPC100998
0.927	High Similarity	NPC476382
0.927	High Similarity	NPC274960
0.927	High Similarity	NPC143120
0.9265	High Similarity	NPC478239
0.9248	High Similarity	NPC157554
0.9248	High Similarity	NPC471988
0.9242	High Similarity	NPC67247
0.9213	High Similarity	NPC246704
0.9191	High Similarity	NPC157816
0.9185	High Similarity	NPC288452
0.9185	High Similarity	NPC267291
0.9185	High Similarity	NPC289690
0.9173	High Similarity	NPC214729
0.9147	High Similarity	NPC147821
0.9147	High Similarity	NPC118787
0.9147	High Similarity	NPC183181
0.9147	High Similarity	NPC292056
0.9147	High Similarity	NPC163332
0.9147	High Similarity	NPC41706
0.9147	High Similarity	NPC319625
0.9147	High Similarity	NPC111247
0.9137	High Similarity	NPC232992
0.913	High Similarity	NPC163898
0.9118	High Similarity	NPC186406
0.9111	High Similarity	NPC226005
0.9111	High Similarity	NPC100389
0.9104	High Similarity	NPC471719
0.9104	High Similarity	NPC120852
0.9077	High Similarity	NPC252307
0.9077	High Similarity	NPC245826
0.9077	High Similarity	NPC474178
0.9071	High Similarity	NPC187398
0.9071	High Similarity	NPC472969
0.9071	High Similarity	NPC476348
0.907	High Similarity	NPC178284
0.907	High Similarity	NPC58607
0.907	High Similarity	NPC191037
0.9065	High Similarity	NPC199928
0.9062	High Similarity	NPC20443
0.9062	High Similarity	NPC60517
0.9062	High Similarity	NPC146886
0.9058	High Similarity	NPC232228
0.9058	High Similarity	NPC110063
0.9051	High Similarity	NPC278469
0.9051	High Similarity	NPC193722
0.9037	High Similarity	NPC281780
0.9015	High Similarity	NPC470096
0.9015	High Similarity	NPC470095
0.9008	High Similarity	NPC86030
0.9008	High Similarity	NPC48315
0.9008	High Similarity	NPC5851
0.9007	High Similarity	NPC476398
0.9007	High Similarity	NPC475250
0.9007	High Similarity	NPC94871
0.9007	High Similarity	NPC259347
0.9007	High Similarity	NPC473427
0.9007	High Similarity	NPC476386
0.9007	High Similarity	NPC471062
0.9007	High Similarity	NPC306890
0.9007	High Similarity	NPC470933
0.9007	High Similarity	NPC106138
0.9	High Similarity	NPC165045
0.9	High Similarity	NPC118533
0.9	High Similarity	NPC476347
0.8993	High Similarity	NPC287615
0.8993	High Similarity	NPC216819
0.8993	High Similarity	NPC83743
0.8993	High Similarity	NPC262182
0.8992	High Similarity	NPC194519
0.8984	High Similarity	NPC471693
0.8978	High Similarity	NPC83375
0.8978	High Similarity	NPC224876
0.8976	High Similarity	NPC470804
0.8976	High Similarity	NPC147654
0.8963	High Similarity	NPC37468
0.8963	High Similarity	NPC186418
0.8955	High Similarity	NPC309744
0.8955	High Similarity	NPC106406
0.8955	High Similarity	NPC886
0.8955	High Similarity	NPC111635
0.8955	High Similarity	NPC287597
0.8955	High Similarity	NPC34293
0.8947	High Similarity	NPC184447
0.8947	High Similarity	NPC35932
0.8947	High Similarity	NPC160991
0.8947	High Similarity	NPC16208
0.8947	High Similarity	NPC7903
0.8944	High Similarity	NPC294522
0.8944	High Similarity	NPC257970
0.8944	High Similarity	NPC188393
0.8944	High Similarity	NPC470934
0.8944	High Similarity	NPC205727
0.8944	High Similarity	NPC120426
0.8944	High Similarity	NPC21184
0.8944	High Similarity	NPC470927
0.8939	High Similarity	NPC187998
0.8939	High Similarity	NPC77040
0.8939	High Similarity	NPC42300
0.8939	High Similarity	NPC174495
0.8939	High Similarity	NPC257582
0.8939	High Similarity	NPC242807
0.8939	High Similarity	NPC153739
0.8939	High Similarity	NPC92164
0.8939	High Similarity	NPC64201
0.8939	High Similarity	NPC241522
0.8939	High Similarity	NPC145305
0.8936	High Similarity	NPC102934
0.8936	High Similarity	NPC252402
0.8931	High Similarity	NPC72529
0.8931	High Similarity	NPC110313
0.8931	High Similarity	NPC109275
0.8929	High Similarity	NPC476865
0.8929	High Similarity	NPC98356
0.8921	High Similarity	NPC292443
0.8915	High Similarity	NPC94276
0.8915	High Similarity	NPC109822
0.8915	High Similarity	NPC48990
0.8915	High Similarity	NPC293701
0.8915	High Similarity	NPC114901
0.8913	High Similarity	NPC131971
0.8905	High Similarity	NPC202700
0.8898	High Similarity	NPC470848
0.8898	High Similarity	NPC470849
0.8898	High Similarity	NPC204466
0.8897	High Similarity	NPC78363
0.8881	High Similarity	NPC475468
0.8873	High Similarity	NPC476394
0.8873	High Similarity	NPC176903
0.8873	High Similarity	NPC98809
0.8873	High Similarity	NPC30688
0.8873	High Similarity	NPC478242
0.8872	High Similarity	NPC248307
0.8872	High Similarity	NPC65942
0.8872	High Similarity	NPC277804
0.8872	High Similarity	NPC472597
0.8865	High Similarity	NPC283081
0.8865	High Similarity	NPC221383
0.8865	High Similarity	NPC143892
0.8865	High Similarity	NPC299090
0.8864	High Similarity	NPC476968
0.8864	High Similarity	NPC475875
0.8864	High Similarity	NPC170844
0.8857	High Similarity	NPC476868
0.8857	High Similarity	NPC476866
0.8857	High Similarity	NPC476869
0.8857	High Similarity	NPC476864
0.8855	High Similarity	NPC5428
0.8846	High Similarity	NPC148627
0.8841	High Similarity	NPC476385
0.8841	High Similarity	NPC100675
0.8841	High Similarity	NPC134405
0.8837	High Similarity	NPC279379
0.8832	High Similarity	NPC64141
0.8832	High Similarity	NPC68092
0.8832	High Similarity	NPC472350
0.8832	High Similarity	NPC89105
0.8832	High Similarity	NPC81515
0.8832	High Similarity	NPC197316
0.8832	High Similarity	NPC476383
0.8828	High Similarity	NPC184651
0.8828	High Similarity	NPC113865
0.8828	High Similarity	NPC54872
0.8828	High Similarity	NPC470212
0.8828	High Similarity	NPC324571
0.8828	High Similarity	NPC343720
0.8828	High Similarity	NPC473853
0.8828	High Similarity	NPC262156
0.8828	High Similarity	NPC70752
0.8828	High Similarity	NPC312675
0.8824	High Similarity	NPC177035
0.8824	High Similarity	NPC52277
0.8824	High Similarity	NPC199459
0.8819	High Similarity	NPC35071
0.8819	High Similarity	NPC202474
0.8819	High Similarity	NPC148615
0.8819	High Similarity	NPC478268
0.8819	High Similarity	NPC177475
0.8819	High Similarity	NPC75695
0.8815	High Similarity	NPC170694
0.8815	High Similarity	NPC310854
0.8815	High Similarity	NPC471110
0.8806	High Similarity	NPC5423

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 NPC135127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	798
0.2-0.3	1755
0.3-0.4	2620
0.4-0.5	1823
0.5-0.6	1031
0.6-0.7	706
0.7-0.8	158
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD3027	Phase 3
0.8832	High Similarity	NPD7266	Discontinued
0.855	High Similarity	NPD4379	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1653	Approved
0.8322	Intermediate Similarity	NPD6190	Approved
0.8261	Intermediate Similarity	NPD1613	Approved
0.8261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD228	Approved
0.8092	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD5536	Phase 2
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7971	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1934	Approved
0.7872	Intermediate Similarity	NPD4060	Phase 1
0.7871	Intermediate Similarity	NPD6234	Discontinued
0.7846	Intermediate Similarity	NPD5283	Phase 1
0.7817	Intermediate Similarity	NPD230	Phase 1
0.7795	Intermediate Similarity	NPD1358	Approved
0.7792	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.775	Intermediate Similarity	NPD3818	Discontinued
0.7742	Intermediate Similarity	NPD3882	Suspended
0.7742	Intermediate Similarity	NPD4966	Approved
0.7742	Intermediate Similarity	NPD4967	Phase 2
0.7742	Intermediate Similarity	NPD4965	Approved
0.7737	Intermediate Similarity	NPD2983	Phase 2
0.7737	Intermediate Similarity	NPD2982	Phase 2
0.7736	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6166	Phase 2
0.7727	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2801	Approved
0.7721	Intermediate Similarity	NPD3705	Approved
0.7702	Intermediate Similarity	NPD7054	Approved
0.7692	Intermediate Similarity	NPD4340	Discontinued
0.7676	Intermediate Similarity	NPD6233	Phase 2
0.7664	Intermediate Similarity	NPD2981	Phase 2
0.7654	Intermediate Similarity	NPD7074	Phase 3
0.7654	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD3496	Discontinued
0.7643	Intermediate Similarity	NPD9494	Approved
0.7643	Intermediate Similarity	NPD3018	Phase 2
0.764	Intermediate Similarity	NPD7228	Approved
0.7632	Intermediate Similarity	NPD3687	Approved
0.7632	Intermediate Similarity	NPD3686	Approved
0.763	Intermediate Similarity	NPD1357	Approved
0.7622	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1558	Phase 1
0.7622	Intermediate Similarity	NPD3620	Phase 2
0.7622	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2935	Discontinued
0.7593	Intermediate Similarity	NPD5844	Phase 1
0.7591	Intermediate Similarity	NPD422	Phase 1
0.759	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3134	Approved
0.7568	Intermediate Similarity	NPD3060	Approved
0.7568	Intermediate Similarity	NPD1652	Phase 2
0.7566	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD8127	Discontinued
0.7538	Intermediate Similarity	NPD3021	Approved
0.7538	Intermediate Similarity	NPD3022	Approved
0.7535	Intermediate Similarity	NPD7095	Approved
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.7518	Intermediate Similarity	NPD2861	Phase 2
0.7517	Intermediate Similarity	NPD6653	Approved
0.7517	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7484	Intermediate Similarity	NPD6386	Approved
0.7484	Intermediate Similarity	NPD6385	Approved
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7483	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD4357	Discontinued
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3455	Phase 2
0.7468	Intermediate Similarity	NPD7075	Discontinued
0.7464	Intermediate Similarity	NPD1091	Approved
0.7463	Intermediate Similarity	NPD7157	Approved
0.7462	Intermediate Similarity	NPD2684	Approved
0.7455	Intermediate Similarity	NPD7251	Discontinued
0.7452	Intermediate Similarity	NPD5402	Approved
0.745	Intermediate Similarity	NPD4237	Approved
0.745	Intermediate Similarity	NPD4236	Phase 3
0.7448	Intermediate Similarity	NPD447	Suspended
0.7448	Intermediate Similarity	NPD6355	Discontinued
0.7445	Intermediate Similarity	NPD4626	Approved
0.7438	Intermediate Similarity	NPD7199	Phase 2
0.7432	Intermediate Similarity	NPD5763	Approved
0.7432	Intermediate Similarity	NPD5762	Approved
0.7431	Intermediate Similarity	NPD4062	Phase 3
0.741	Intermediate Similarity	NPD7808	Phase 3
0.74	Intermediate Similarity	NPD8166	Discontinued
0.7389	Intermediate Similarity	NPD2977	Approved
0.7389	Intermediate Similarity	NPD2978	Approved
0.7386	Intermediate Similarity	NPD1512	Approved
0.7386	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5691	Approved
0.7368	Intermediate Similarity	NPD5535	Approved
0.7368	Intermediate Similarity	NPD6799	Approved
0.7362	Intermediate Similarity	NPD7473	Discontinued
0.7358	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7038	Approved
0.7349	Intermediate Similarity	NPD7039	Approved
0.7347	Intermediate Similarity	NPD4536	Approved
0.7347	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4538	Approved
0.7343	Intermediate Similarity	NPD4908	Phase 1
0.7338	Intermediate Similarity	NPD5403	Approved
0.7333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6674	Discontinued
0.7333	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7325	Intermediate Similarity	NPD6801	Discontinued
0.732	Intermediate Similarity	NPD3536	Discontinued
0.7299	Intermediate Similarity	NPD9545	Approved
0.7299	Intermediate Similarity	NPD1548	Phase 1
0.7297	Intermediate Similarity	NPD7033	Discontinued
0.7286	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3847	Discontinued
0.726	Intermediate Similarity	NPD4140	Approved
0.7252	Intermediate Similarity	NPD290	Approved
0.7248	Intermediate Similarity	NPD6032	Approved
0.7248	Intermediate Similarity	NPD2438	Suspended
0.7246	Intermediate Similarity	NPD6559	Discontinued
0.7246	Intermediate Similarity	NPD5585	Approved
0.7241	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7097	Phase 1
0.7219	Intermediate Similarity	NPD4162	Approved
0.7214	Intermediate Similarity	NPD1535	Discovery
0.7214	Intermediate Similarity	NPD1610	Phase 2
0.7208	Intermediate Similarity	NPD5401	Approved
0.7208	Intermediate Similarity	NPD4123	Phase 3
0.7202	Intermediate Similarity	NPD7549	Discontinued
0.72	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1778	Approved
0.7192	Intermediate Similarity	NPD2674	Phase 3
0.719	Intermediate Similarity	NPD5058	Phase 3
0.7183	Intermediate Similarity	NPD3225	Approved
0.7181	Intermediate Similarity	NPD5588	Approved
0.7181	Intermediate Similarity	NPD5960	Phase 3
0.7176	Intermediate Similarity	NPD968	Approved
0.7174	Intermediate Similarity	NPD1894	Discontinued
0.7171	Intermediate Similarity	NPD3750	Approved
0.717	Intermediate Similarity	NPD8455	Phase 2
0.717	Intermediate Similarity	NPD7819	Suspended
0.7163	Intermediate Similarity	NPD1481	Phase 2
0.7161	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5242	Approved
0.7133	Intermediate Similarity	NPD2797	Approved
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7132	Intermediate Similarity	NPD291	Approved
0.7125	Intermediate Similarity	NPD5353	Approved
0.7124	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2677	Approved
0.7123	Intermediate Similarity	NPD3764	Approved
0.7113	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5177	Phase 3
0.7103	Intermediate Similarity	NPD6832	Phase 2
0.7103	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1933	Approved
0.7089	Intermediate Similarity	NPD6599	Discontinued
0.7089	Intermediate Similarity	NPD4678	Approved
0.7089	Intermediate Similarity	NPD4675	Approved
0.7086	Intermediate Similarity	NPD1375	Discontinued
0.7086	Intermediate Similarity	NPD3540	Phase 1
0.7083	Intermediate Similarity	NPD6584	Phase 3
0.708	Intermediate Similarity	NPD6671	Approved
0.7075	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD17	Approved
0.7071	Intermediate Similarity	NPD6516	Phase 2
0.7071	Intermediate Similarity	NPD5846	Approved
0.7067	Intermediate Similarity	NPD1510	Phase 2
0.7063	Intermediate Similarity	NPD8651	Approved
0.7063	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4666	Phase 3
0.7055	Intermediate Similarity	NPD5494	Approved
0.7051	Intermediate Similarity	NPD6273	Approved
0.7044	Intermediate Similarity	NPD7411	Suspended
0.7042	Intermediate Similarity	NPD2235	Phase 2
0.7042	Intermediate Similarity	NPD2231	Phase 2
0.7042	Intermediate Similarity	NPD9269	Phase 2
0.7039	Intermediate Similarity	NPD1549	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