NPASS Compound

Structure

NPC267091 OpenBabel07101718302D 35 38 0 0 1 0 0 0 0 0999 V2000 -4.3729 -4.6634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1582 -1.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7816 -4.0778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2464 -2.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7327 -3.7688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1974 -2.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1527 -1.9228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9771 -3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5704 -2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0385 -3.4087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9406 -2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5594 -2.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9716 -3.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0874 -3.7177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8916 -2.4816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5540 -2.9408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8795 -4.6958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3784 -4.5589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.5933 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 1.3443 -3.0485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 9 2 0 0 0 0 3 16 1 0 0 0 0 4 7 1 0 0 0 0 4 17 2 0 0 0 0 5 8 2 0 0 0 0 5 17 1 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 20 2 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 18 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 34 1 0 0 0 0 15 35 1 0 0 0 0 17 27 1 0 0 0 0 19 11 1 6 0 0 0 19 21 1 0 0 0 0 20 28 1 0 0 0 0 21 15 1 6 0 0 0 21 26 1 0 0 0 0 22 24 2 0 0 0 0 22 29 1 0 0 0 0 23 25 2 0 0 0 0 23 30 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 18 1 1 0 0 0 26 34 1 0 0 0 0 27 31 2 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.18
Volume:	485.279
LogP:	4.095
LogD:	3.699
LogS:	-3.846
# Rotatable Bonds:	9
TPSA:	114.68
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.411
Synthetic Accessibility Score:	3.537
Fsp3:	0.296
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:	-5.031
MDCK Permeability:	1.4514300346490927e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	98.88514709472656%
Volume Distribution (VD):	0.638
Pgp-substrate:	2.7335455417633057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.65
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.898
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.873
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.471

ADMET: Excretion

Clearance (CL):	13.296
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.247
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.401
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.181
Skin Sensitization:	0.934
Carcinogencity:	0.564
Eye Corrosion:	0.003
Eye Irritation:	0.933
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC267091

Natural Product ID:	NPC267091
*Common Name:**	Agastinol
IUPAC Name:	[(2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl 4-hydroxybenzoate
Synonyms:	agastinol
Standard InCHIKey:	GFXHOKACHHWSQG-KCPMXOJXSA-N
Standard InCHI:	InChI=1S/C27H28O8/c1-32-24-12-16(3-9-22(24)29)11-19-14-34-26(18-6-10-23(30)25(13-18)33-2)21(19)15-35-27(31)17-4-7-20(28)8-5-17/h3-10,12-13,19,21,26,28-30H,11,14-15H2,1-2H3/t19-,21-,26+/m1/s1
SMILES:	COc1cc(ccc1O)[C@@H]1OC[C@H]([C@H]1COC(=O)c1ccc(cc1)O)Cc1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517327
PubChem CID:	637406
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26351	Agastache rugosa	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	15.2	ug.mL-1	PMID[573928]

☑ 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 NPC267091 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	330
0.1-0.2	1220
0.2-0.3	2794
0.3-0.4	6482
0.4-0.5	11041
0.5-0.6	4916
0.6-0.7	5530
0.7-0.8	9027
0.8-0.85	1144
0.85-0.9	201
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC243891
0.9474	High Similarity	NPC469889
0.9351	High Similarity	NPC45943
0.9329	High Similarity	NPC476434
0.9306	High Similarity	NPC67467
0.9221	High Similarity	NPC216916
0.9205	High Similarity	NPC469888
0.9189	High Similarity	NPC472969
0.9128	High Similarity	NPC98809
0.9128	High Similarity	NPC476394
0.9103	High Similarity	NPC223006
0.9103	High Similarity	NPC134047
0.9103	High Similarity	NPC173729
0.9103	High Similarity	NPC272750
0.9057	High Similarity	NPC180768
0.9038	High Similarity	NPC144557
0.9032	High Similarity	NPC53889
0.9026	High Similarity	NPC226759
0.902	High Similarity	NPC203757
0.8973	High Similarity	NPC100675
0.8968	High Similarity	NPC87317
0.8954	High Similarity	NPC25127
0.8954	High Similarity	NPC287504
0.8947	High Similarity	NPC75695
0.8944	High Similarity	NPC316539
0.8933	High Similarity	NPC102934
0.8933	High Similarity	NPC252402
0.8931	High Similarity	NPC311912
0.8926	High Similarity	NPC30890
0.8919	High Similarity	NPC469615
0.8919	High Similarity	NPC473090
0.8917	High Similarity	NPC42797
0.8917	High Similarity	NPC473445
0.891	High Similarity	NPC476373
0.8903	High Similarity	NPC289322
0.8903	High Similarity	NPC133984
0.8903	High Similarity	NPC143328
0.8903	High Similarity	NPC114179
0.8903	High Similarity	NPC160512
0.8903	High Similarity	NPC156818
0.8903	High Similarity	NPC68324
0.8903	High Similarity	NPC38779
0.8897	High Similarity	NPC281780
0.8896	High Similarity	NPC300757
0.8896	High Similarity	NPC180901
0.8896	High Similarity	NPC145425
0.8889	High Similarity	NPC44730
0.8889	High Similarity	NPC131121
0.8889	High Similarity	NPC295646
0.8875	High Similarity	NPC88557
0.8868	High Similarity	NPC43065
0.8861	High Similarity	NPC89131
0.8861	High Similarity	NPC291977
0.8861	High Similarity	NPC100420
0.8859	High Similarity	NPC469683
0.8859	High Similarity	NPC223185
0.8844	High Similarity	NPC326065
0.8839	High Similarity	NPC104983
0.8839	High Similarity	NPC471405
0.8839	High Similarity	NPC291948
0.8839	High Similarity	NPC88803
0.8839	High Similarity	NPC300845
0.8839	High Similarity	NPC250436
0.8831	High Similarity	NPC327032
0.8831	High Similarity	NPC191046
0.8831	High Similarity	NPC194095
0.8828	High Similarity	NPC90431
0.8828	High Similarity	NPC471988
0.8824	High Similarity	NPC151425
0.8819	High Similarity	NPC67247
0.8816	High Similarity	NPC473091
0.8816	High Similarity	NPC261322
0.88	High Similarity	NPC9370
0.88	High Similarity	NPC287495
0.8797	High Similarity	NPC476372
0.8797	High Similarity	NPC476371
0.8792	High Similarity	NPC46161
0.8792	High Similarity	NPC160378
0.8792	High Similarity	NPC239608
0.879	High Similarity	NPC24627
0.879	High Similarity	NPC24164
0.879	High Similarity	NPC472962
0.879	High Similarity	NPC472961
0.8784	High Similarity	NPC253722
0.8784	High Similarity	NPC31751
0.8784	High Similarity	NPC253481
0.8782	High Similarity	NPC35598
0.8782	High Similarity	NPC222689
0.8782	High Similarity	NPC472860
0.8776	High Similarity	NPC288452
0.8776	High Similarity	NPC289690
0.8774	High Similarity	NPC10205
0.8766	High Similarity	NPC157898
0.8766	High Similarity	NPC474656
0.8765	High Similarity	NPC247964
0.8758	High Similarity	NPC216403
0.8758	High Similarity	NPC21956
0.8758	High Similarity	NPC41494
0.8758	High Similarity	NPC202428
0.8758	High Similarity	NPC300329
0.8758	High Similarity	NPC186100
0.8758	High Similarity	NPC266545
0.8758	High Similarity	NPC62354
0.8742	High Similarity	NPC100425
0.8725	High Similarity	NPC477697
0.8725	High Similarity	NPC470811
0.8725	High Similarity	NPC106920
0.8725	High Similarity	NPC477696
0.8725	High Similarity	NPC273657
0.8718	High Similarity	NPC470896
0.8718	High Similarity	NPC473275
0.8718	High Similarity	NPC227062
0.8718	High Similarity	NPC318432
0.871	High Similarity	NPC62051
0.8701	High Similarity	NPC163883
0.8701	High Similarity	NPC124842
0.8701	High Similarity	NPC134905
0.8701	High Similarity	NPC270268
0.8701	High Similarity	NPC93498
0.8701	High Similarity	NPC36130
0.8701	High Similarity	NPC478268
0.8699	High Similarity	NPC120852
0.8696	High Similarity	NPC177362
0.8693	High Similarity	NPC221091
0.8693	High Similarity	NPC259576
0.869	High Similarity	NPC176814
0.869	High Similarity	NPC135127
0.869	High Similarity	NPC68779
0.869	High Similarity	NPC300776
0.869	High Similarity	NPC4982
0.869	High Similarity	NPC5310
0.8688	High Similarity	NPC475738
0.8688	High Similarity	NPC142614
0.8688	High Similarity	NPC471788
0.8684	High Similarity	NPC236166
0.8684	High Similarity	NPC1580
0.8679	High Similarity	NPC33298
0.8679	High Similarity	NPC76687
0.8679	High Similarity	NPC246024
0.8679	High Similarity	NPC285108
0.8675	High Similarity	NPC98356
0.8671	High Similarity	NPC203020
0.8671	High Similarity	NPC300680
0.8671	High Similarity	NPC239818
0.8671	High Similarity	NPC218471
0.8671	High Similarity	NPC239966
0.8667	High Similarity	NPC46880
0.8662	High Similarity	NPC167098
0.8662	High Similarity	NPC296044
0.865	High Similarity	NPC469506
0.8649	High Similarity	NPC147379
0.8645	High Similarity	NPC19380
0.8645	High Similarity	NPC61604
0.8645	High Similarity	NPC137813
0.8645	High Similarity	NPC178574
0.8645	High Similarity	NPC146277
0.8645	High Similarity	NPC245615
0.8645	High Similarity	NPC65591
0.8645	High Similarity	NPC299706
0.8645	High Similarity	NPC308555
0.8645	High Similarity	NPC115466
0.8645	High Similarity	NPC115203
0.8634	High Similarity	NPC83049
0.8634	High Similarity	NPC118162
0.8634	High Similarity	NPC200726
0.8634	High Similarity	NPC320471
0.863	High Similarity	NPC113295
0.8627	High Similarity	NPC474903
0.8627	High Similarity	NPC125570
0.8627	High Similarity	NPC111785
0.8621	High Similarity	NPC159418
0.8621	High Similarity	NPC283823
0.8618	High Similarity	NPC283081
0.8618	High Similarity	NPC299090
0.8618	High Similarity	NPC24257
0.8618	High Similarity	NPC153620
0.8618	High Similarity	NPC229264
0.8618	High Similarity	NPC221383
0.8618	High Similarity	NPC143892
0.8616	High Similarity	NPC92589
0.8609	High Similarity	NPC163898
0.8608	High Similarity	NPC179914
0.8608	High Similarity	NPC160780
0.8608	High Similarity	NPC76211
0.8608	High Similarity	NPC289811
0.86	High Similarity	NPC229218
0.86	High Similarity	NPC141817
0.86	High Similarity	NPC169214
0.86	High Similarity	NPC192597
0.86	High Similarity	NPC176030
0.8599	High Similarity	NPC150227
0.8599	High Similarity	NPC165483
0.8591	High Similarity	NPC29599
0.8591	High Similarity	NPC9218
0.8591	High Similarity	NPC28398
0.859	High Similarity	NPC144801
0.859	High Similarity	NPC43872
0.859	High Similarity	NPC116850
0.859	High Similarity	NPC291510
0.859	High Similarity	NPC197188

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 NPC267091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	783
0.2-0.3	1508
0.3-0.4	2417
0.4-0.5	2176
0.5-0.6	1185
0.6-0.7	625
0.7-0.8	157
0.8-0.85	23
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD4868	Clinical (unspecified phase)
0.8733	High Similarity	NPD6143	Clinical (unspecified phase)
0.8562	High Similarity	NPD6980	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD4628	Phase 3
0.8408	Intermediate Similarity	NPD1934	Approved
0.8393	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6234	Discontinued
0.8373	Intermediate Similarity	NPD7685	Pre-registration
0.8355	Intermediate Similarity	NPD6190	Approved
0.8354	Intermediate Similarity	NPD3818	Discontinued
0.8344	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8303	Intermediate Similarity	NPD5844	Phase 1
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.825	Intermediate Similarity	NPD3882	Suspended
0.8239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD37	Approved
0.816	Intermediate Similarity	NPD7199	Phase 2
0.8137	Intermediate Similarity	NPD4966	Approved
0.8137	Intermediate Similarity	NPD4965	Approved
0.8137	Intermediate Similarity	NPD4967	Phase 2
0.8125	Intermediate Similarity	NPD1465	Phase 2
0.8125	Intermediate Similarity	NPD2801	Approved
0.8121	Intermediate Similarity	NPD230	Phase 1
0.8105	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3764	Approved
0.8036	Intermediate Similarity	NPD7074	Phase 3
0.8035	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD5494	Approved
0.7976	Intermediate Similarity	NPD7054	Approved
0.7975	Intermediate Similarity	NPD7075	Discontinued
0.7959	Intermediate Similarity	NPD9494	Approved
0.7937	Intermediate Similarity	NPD4380	Phase 2
0.7929	Intermediate Similarity	NPD7472	Approved
0.7898	Intermediate Similarity	NPD1511	Approved
0.7895	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7266	Discontinued
0.7852	Intermediate Similarity	NPD3027	Phase 3
0.7848	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD8127	Discontinued
0.7808	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1512	Approved
0.7792	Intermediate Similarity	NPD2935	Discontinued
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7791	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6386	Approved
0.7778	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD6385	Approved
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7758	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6233	Phase 2
0.7744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1608	Approved
0.7733	Intermediate Similarity	NPD7251	Discontinued
0.7733	Intermediate Similarity	NPD6559	Discontinued
0.773	Intermediate Similarity	NPD6801	Discontinued
0.7707	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4110	Phase 3
0.7707	Intermediate Similarity	NPD8166	Discontinued
0.7692	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6273	Approved
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7682	Intermediate Similarity	NPD6798	Discontinued
0.7673	Intermediate Similarity	NPD6799	Approved
0.7654	Intermediate Similarity	NPD7458	Discontinued
0.7647	Intermediate Similarity	NPD6355	Discontinued
0.7639	Intermediate Similarity	NPD9545	Approved
0.7633	Intermediate Similarity	NPD5242	Approved
0.763	Intermediate Similarity	NPD7038	Approved
0.763	Intermediate Similarity	NPD7039	Approved
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7614	Intermediate Similarity	NPD8434	Phase 2
0.7613	Intermediate Similarity	NPD1510	Phase 2
0.7607	Intermediate Similarity	NPD6599	Discontinued
0.7595	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD7768	Phase 2
0.7588	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1549	Phase 2
0.7546	Intermediate Similarity	NPD3455	Phase 2
0.7546	Intermediate Similarity	NPD3226	Approved
0.7546	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3749	Approved
0.7543	Intermediate Similarity	NPD8313	Approved
0.7543	Intermediate Similarity	NPD8312	Approved
0.7534	Intermediate Similarity	NPD17	Approved
0.7532	Intermediate Similarity	NPD447	Suspended
0.753	Intermediate Similarity	NPD5353	Approved
0.753	Intermediate Similarity	NPD5402	Approved
0.7529	Intermediate Similarity	NPD7240	Approved
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.7485	Intermediate Similarity	NPD1653	Approved
0.7484	Intermediate Similarity	NPD7003	Approved
0.747	Intermediate Similarity	NPD8455	Phase 2
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1240	Approved
0.7468	Intermediate Similarity	NPD1613	Approved
0.7452	Intermediate Similarity	NPD2796	Approved
0.7452	Intermediate Similarity	NPD2438	Suspended
0.7451	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5403	Approved
0.7407	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2344	Approved
0.7401	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2799	Discontinued
0.7389	Intermediate Similarity	NPD7033	Discontinued
0.7386	Intermediate Similarity	NPD7095	Approved
0.7383	Intermediate Similarity	NPD9269	Phase 2
0.7372	Intermediate Similarity	NPD1607	Approved
0.7368	Intermediate Similarity	NPD7229	Phase 3
0.7356	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4060	Phase 1
0.7355	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3620	Phase 2
0.7355	Intermediate Similarity	NPD943	Approved
0.7351	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD3268	Approved
0.7329	Intermediate Similarity	NPD5536	Phase 2
0.732	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD1933	Approved
0.7301	Intermediate Similarity	NPD5401	Approved
0.7292	Intermediate Similarity	NPD5283	Phase 1
0.7285	Intermediate Similarity	NPD1283	Approved
0.7284	Intermediate Similarity	NPD7440	Discontinued
0.7278	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3972	Approved
0.7261	Intermediate Similarity	NPD6653	Approved
0.7255	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2861	Phase 2
0.7246	Intermediate Similarity	NPD6873	Phase 2
0.7244	Intermediate Similarity	NPD2979	Phase 3
0.7234	Intermediate Similarity	NPD7680	Approved
0.7233	Intermediate Similarity	NPD1551	Phase 2
0.7222	Intermediate Similarity	NPD2354	Approved
0.7222	Intermediate Similarity	NPD2309	Approved
0.7222	Intermediate Similarity	NPD3887	Approved
0.7209	Intermediate Similarity	NPD1247	Approved
0.7208	Intermediate Similarity	NPD6832	Phase 2
0.7208	Intermediate Similarity	NPD4908	Phase 1
0.7204	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7177	Discontinued
0.72	Intermediate Similarity	NPD3705	Approved
0.719	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2798	Approved
0.7188	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6004	Phase 3
0.7188	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6002	Phase 3
0.7188	Intermediate Similarity	NPD6005	Phase 3
0.7188	Intermediate Similarity	NPD2346	Discontinued
0.7186	Intermediate Similarity	NPD7028	Phase 2
0.7179	Intermediate Similarity	NPD4062	Phase 3
0.7171	Intermediate Similarity	NPD1876	Approved
0.717	Intermediate Similarity	NPD4308	Phase 3
0.7161	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD5958	Discontinued
0.7135	Intermediate Similarity	NPD6971	Discontinued
0.7125	Intermediate Similarity	NPD5404	Approved
0.7125	Intermediate Similarity	NPD5406	Approved
0.7125	Intermediate Similarity	NPD5405	Approved
0.7125	Intermediate Similarity	NPD5408	Approved
0.7124	Intermediate Similarity	NPD1203	Approved
0.7118	Intermediate Similarity	NPD5978	Approved
0.7118	Intermediate Similarity	NPD5977	Approved
0.7115	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2313	Discontinued
0.7114	Intermediate Similarity	NPD9268	Approved
0.7108	Intermediate Similarity	NPD920	Approved
0.7107	Intermediate Similarity	NPD7097	Phase 1
0.7102	Intermediate Similarity	NPD3751	Discontinued
0.7095	Intermediate Similarity	NPD7549	Discontinued
0.7091	Intermediate Similarity	NPD3146	Approved
0.7091	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1281	Approved
0.707	Intermediate Similarity	NPD6663	Approved
0.7069	Intermediate Similarity	NPD5711	Approved
0.7069	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD5760	Phase 2
0.7059	Intermediate Similarity	NPD5761	Phase 2
0.7055	Intermediate Similarity	NPD1878	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