NPASS Compound

Structure

NPC243891 OpenBabel07101719512D 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 0 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 11 19 2 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 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:	478.16
Volume:	482.643
LogP:	3.819
LogD:	3.355
LogS:	-3.805
# Rotatable Bonds:	8
TPSA:	114.68
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	3.467
Fsp3:	0.222
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:	-4.979
MDCK Permeability:	1.3426979421637952e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.232
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.291

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	99.07764434814453%
Volume Distribution (VD):	0.563
Pgp-substrate:	2.52931809425354%

ADMET: Metabolism

CYP1A2-inhibitor:	0.49
CYP1A2-substrate:	0.769
CYP2C19-inhibitor:	0.467
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.713
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.509
CYP3A4-inhibitor:	0.717
CYP3A4-substrate:	0.388

ADMET: Excretion

Clearance (CL):	11.274
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.22
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.387
AMES Toxicity:	0.31
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.952
Carcinogencity:	0.835
Eye Corrosion:	0.003
Eye Irritation:	0.857
Respiratory Toxicity:	0.373

Download Data

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

Natural Product: NPC243891

Natural Product ID:	NPC243891
*Common Name:**	Agastenol
IUPAC Name:	[(2R,3S,4E)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]oxolan-3-yl]methyl 4-hydroxybenzoate
Synonyms:	agastenol
Standard InCHIKey:	NYOJCGUMMQIVQV-HPMYTTEASA-N
Standard InCHI:	InChI=1S/C27H26O8/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/h3-13,21,26,28-30H,14-15H2,1-2H3/b19-11-/t21-,26+/m1/s1
SMILES:	COc1cc(ccc1O)/C=C1/CO[C@@H](c2ccc(c(c2)OC)O)[C@@H]1COC(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464349
PubChem CID:	10073783
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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	=	11.4	ug.mL-1	PMID[520099]

☑ 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 NPC243891 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	327
0.1-0.2	1240
0.2-0.3	2856
0.3-0.4	6832
0.4-0.5	10876
0.5-0.6	4732
0.6-0.7	5747
0.7-0.8	8777
0.8-0.85	1094
0.85-0.9	203
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC267091
0.9408	High Similarity	NPC469889
0.9286	High Similarity	NPC45943
0.9267	High Similarity	NPC469888
0.9262	High Similarity	NPC476434
0.9252	High Similarity	NPC472969
0.9236	High Similarity	NPC67467
0.9189	High Similarity	NPC98809
0.9189	High Similarity	NPC476394
0.9156	High Similarity	NPC216916
0.9091	High Similarity	NPC53889
0.9085	High Similarity	NPC226759
0.9038	High Similarity	NPC173729
0.9038	High Similarity	NPC223006
0.9038	High Similarity	NPC272750
0.9038	High Similarity	NPC134047
0.9026	High Similarity	NPC87317
0.9007	High Similarity	NPC75695
0.8994	High Similarity	NPC180768
0.898	High Similarity	NPC473090
0.898	High Similarity	NPC469615
0.8974	High Similarity	NPC144557
0.8968	High Similarity	NPC476373
0.8961	High Similarity	NPC133984
0.8961	High Similarity	NPC38779
0.8961	High Similarity	NPC114179
0.8961	High Similarity	NPC156818
0.8961	High Similarity	NPC289322
0.8961	High Similarity	NPC160512
0.8961	High Similarity	NPC68324
0.8954	High Similarity	NPC145425
0.8954	High Similarity	NPC203757
0.8947	High Similarity	NPC44730
0.8919	High Similarity	NPC469683
0.8904	High Similarity	NPC100675
0.8904	High Similarity	NPC326065
0.8896	High Similarity	NPC104983
0.8896	High Similarity	NPC471405
0.8896	High Similarity	NPC291948
0.8896	High Similarity	NPC300845
0.8896	High Similarity	NPC88803
0.8896	High Similarity	NPC250436
0.8889	High Similarity	NPC25127
0.8889	High Similarity	NPC191046
0.8889	High Similarity	NPC287504
0.8889	High Similarity	NPC194095
0.8889	High Similarity	NPC90431
0.8889	High Similarity	NPC327032
0.8882	High Similarity	NPC316539
0.8874	High Similarity	NPC473091
0.8868	High Similarity	NPC311912
0.8867	High Similarity	NPC102934
0.8867	High Similarity	NPC252402
0.8859	High Similarity	NPC287495
0.8859	High Similarity	NPC9370
0.8859	High Similarity	NPC30890
0.8854	High Similarity	NPC476371
0.8854	High Similarity	NPC473445
0.8854	High Similarity	NPC42797
0.8854	High Similarity	NPC476372
0.8851	High Similarity	NPC160378
0.8846	High Similarity	NPC24164
0.8839	High Similarity	NPC35598
0.8839	High Similarity	NPC472860
0.8839	High Similarity	NPC143328
0.8839	High Similarity	NPC222689
0.8836	High Similarity	NPC289690
0.8836	High Similarity	NPC288452
0.8831	High Similarity	NPC300757
0.8831	High Similarity	NPC10205
0.8831	High Similarity	NPC180901
0.8828	High Similarity	NPC281780
0.8824	High Similarity	NPC295646
0.8824	High Similarity	NPC131121
0.8824	High Similarity	NPC474656
0.8824	High Similarity	NPC157898
0.882	High Similarity	NPC247964
0.8816	High Similarity	NPC300329
0.8812	High Similarity	NPC88557
0.8805	High Similarity	NPC43065
0.8797	High Similarity	NPC100420
0.8797	High Similarity	NPC291977
0.8797	High Similarity	NPC89131
0.8792	High Similarity	NPC223185
0.8774	High Similarity	NPC318432
0.8774	High Similarity	NPC473275
0.8774	High Similarity	NPC470896
0.8759	High Similarity	NPC471988
0.8758	High Similarity	NPC93498
0.8758	High Similarity	NPC151425
0.8758	High Similarity	NPC163883
0.8758	High Similarity	NPC36130
0.8758	High Similarity	NPC134905
0.875	High Similarity	NPC259576
0.875	High Similarity	NPC261322
0.875	High Similarity	NPC135127
0.875	High Similarity	NPC67247
0.875	High Similarity	NPC221091
0.8742	High Similarity	NPC142614
0.8742	High Similarity	NPC471788
0.8742	High Similarity	NPC1580
0.8734	High Similarity	NPC285108
0.8734	High Similarity	NPC33298
0.8734	High Similarity	NPC246024
0.8733	High Similarity	NPC98356
0.8726	High Similarity	NPC472962
0.8726	High Similarity	NPC24627
0.8726	High Similarity	NPC239966
0.8726	High Similarity	NPC203020
0.8726	High Similarity	NPC472961
0.8725	High Similarity	NPC239608
0.8725	High Similarity	NPC46161
0.8716	High Similarity	NPC253481
0.8716	High Similarity	NPC253722
0.8716	High Similarity	NPC31751
0.8701	High Similarity	NPC19380
0.8701	High Similarity	NPC146277
0.8701	High Similarity	NPC137813
0.8696	High Similarity	NPC266545
0.8696	High Similarity	NPC21956
0.8696	High Similarity	NPC202428
0.8696	High Similarity	NPC216403
0.8696	High Similarity	NPC41494
0.8696	High Similarity	NPC186100
0.8693	High Similarity	NPC62354
0.8684	High Similarity	NPC111785
0.8681	High Similarity	NPC283823
0.8681	High Similarity	NPC159418
0.8679	High Similarity	NPC100425
0.8675	High Similarity	NPC299090
0.8675	High Similarity	NPC283081
0.8675	High Similarity	NPC153620
0.8675	High Similarity	NPC24257
0.8675	High Similarity	NPC229264
0.8675	High Similarity	NPC221383
0.8675	High Similarity	NPC143892
0.8662	High Similarity	NPC160780
0.8662	High Similarity	NPC289811
0.8658	High Similarity	NPC470811
0.8658	High Similarity	NPC273657
0.8658	High Similarity	NPC106920
0.8658	High Similarity	NPC477697
0.8658	High Similarity	NPC477696
0.8654	High Similarity	NPC227062
0.8649	High Similarity	NPC9218
0.8645	High Similarity	NPC62051
0.8642	High Similarity	NPC476365
0.8639	High Similarity	NPC284409
0.8636	High Similarity	NPC478268
0.8636	High Similarity	NPC124842
0.8636	High Similarity	NPC270268
0.8634	High Similarity	NPC177362
0.8634	High Similarity	NPC473818
0.863	High Similarity	NPC120852
0.8627	High Similarity	NPC306343
0.8625	High Similarity	NPC475738
0.8621	High Similarity	NPC68779
0.8621	High Similarity	NPC5310
0.8621	High Similarity	NPC4982
0.8621	High Similarity	NPC106406
0.8621	High Similarity	NPC176814
0.8621	High Similarity	NPC300776
0.8618	High Similarity	NPC236166
0.8618	High Similarity	NPC98009
0.8618	High Similarity	NPC142528
0.8616	High Similarity	NPC76687
0.8611	High Similarity	NPC111888
0.8609	High Similarity	NPC213482
0.8608	High Similarity	NPC239818
0.8608	High Similarity	NPC292415
0.8608	High Similarity	NPC289346
0.8608	High Similarity	NPC300680
0.8608	High Similarity	NPC218471
0.86	High Similarity	NPC46880
0.86	High Similarity	NPC226738
0.86	High Similarity	NPC190587
0.86	High Similarity	NPC121573
0.86	High Similarity	NPC22176
0.8599	High Similarity	NPC1913
0.8599	High Similarity	NPC108456
0.8599	High Similarity	NPC296044
0.8599	High Similarity	NPC167098
0.859	High Similarity	NPC131532
0.8589	High Similarity	NPC469506
0.8581	High Similarity	NPC245615
0.8581	High Similarity	NPC299706
0.8581	High Similarity	NPC115466
0.8581	High Similarity	NPC147379
0.8581	High Similarity	NPC65591
0.8581	High Similarity	NPC61604
0.8581	High Similarity	NPC474784
0.8581	High Similarity	NPC178574
0.8581	High Similarity	NPC308555
0.8581	High Similarity	NPC115203
0.8571	High Similarity	NPC118162
0.8571	High Similarity	NPC32079
0.8571	High Similarity	NPC126206
0.8571	High Similarity	NPC83049
0.8571	High Similarity	NPC200726
0.8571	High Similarity	NPC320471

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 NPC243891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	782
0.2-0.3	1533
0.3-0.4	2439
0.4-0.5	2172
0.5-0.6	1168
0.6-0.7	607
0.7-0.8	158
0.8-0.85	17
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8896	High Similarity	NPD4868	Clinical (unspecified phase)
0.8792	High Similarity	NPD6143	Clinical (unspecified phase)
0.8618	High Similarity	NPD6980	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1934	Approved
0.8411	Intermediate Similarity	NPD6190	Approved
0.8405	Intermediate Similarity	NPD3818	Discontinued
0.8395	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD6166	Phase 2
0.8344	Intermediate Similarity	NPD4628	Phase 3
0.8333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6234	Discontinued
0.8313	Intermediate Similarity	NPD7685	Pre-registration
0.8302	Intermediate Similarity	NPD3882	Suspended
0.8291	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6232	Discontinued
0.8253	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8239	Intermediate Similarity	NPD3817	Phase 2
0.8232	Intermediate Similarity	NPD7473	Discontinued
0.8176	Intermediate Similarity	NPD2801	Approved
0.8176	Intermediate Similarity	NPD230	Phase 1
0.8158	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD37	Approved
0.8098	Intermediate Similarity	NPD7199	Phase 2
0.8084	Intermediate Similarity	NPD7074	Phase 3
0.8075	Intermediate Similarity	NPD4965	Approved
0.8075	Intermediate Similarity	NPD4966	Approved
0.8075	Intermediate Similarity	NPD4967	Phase 2
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.8025	Intermediate Similarity	NPD7075	Discontinued
0.8024	Intermediate Similarity	NPD7054	Approved
0.8014	Intermediate Similarity	NPD9494	Approved
0.8	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7977	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7472	Approved
0.7973	Intermediate Similarity	NPD3764	Approved
0.7964	Intermediate Similarity	NPD7228	Approved
0.7949	Intermediate Similarity	NPD1511	Approved
0.7941	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD5494	Approved
0.7908	Intermediate Similarity	NPD7266	Discontinued
0.7905	Intermediate Similarity	NPD3027	Phase 3
0.7862	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1512	Approved
0.7843	Intermediate Similarity	NPD2935	Discontinued
0.784	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6386	Approved
0.7826	Intermediate Similarity	NPD7411	Suspended
0.7826	Intermediate Similarity	NPD6385	Approved
0.7824	Intermediate Similarity	NPD6797	Phase 2
0.7805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6233	Phase 2
0.7785	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD6801	Discontinued
0.7771	Intermediate Similarity	NPD8127	Discontinued
0.7733	Intermediate Similarity	NPD6798	Discontinued
0.7733	Intermediate Similarity	NPD7808	Phase 3
0.773	Intermediate Similarity	NPD7819	Suspended
0.7722	Intermediate Similarity	NPD6799	Approved
0.7692	Intermediate Similarity	NPD9545	Approved
0.7683	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7038	Approved
0.7674	Intermediate Similarity	NPD7039	Approved
0.7671	Intermediate Similarity	NPD1608	Approved
0.7662	Intermediate Similarity	NPD1510	Phase 2
0.7643	Intermediate Similarity	NPD4110	Phase 3
0.7643	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD8166	Discontinued
0.7628	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1549	Phase 2
0.7625	Intermediate Similarity	NPD6273	Approved
0.7593	Intermediate Similarity	NPD3455	Phase 2
0.7593	Intermediate Similarity	NPD7458	Discontinued
0.7582	Intermediate Similarity	NPD447	Suspended
0.7582	Intermediate Similarity	NPD6355	Discontinued
0.7576	Intermediate Similarity	NPD5353	Approved
0.7576	Intermediate Similarity	NPD5402	Approved
0.7574	Intermediate Similarity	NPD5242	Approved
0.7564	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2534	Approved
0.7562	Intermediate Similarity	NPD2532	Approved
0.7562	Intermediate Similarity	NPD2533	Approved
0.7557	Intermediate Similarity	NPD8434	Phase 2
0.7546	Intermediate Similarity	NPD6599	Discontinued
0.7545	Intermediate Similarity	NPD919	Approved
0.7532	Intermediate Similarity	NPD3750	Approved
0.7531	Intermediate Similarity	NPD1653	Approved
0.753	Intermediate Similarity	NPD7768	Phase 2
0.7529	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1240	Approved
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7485	Intermediate Similarity	NPD3749	Approved
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3226	Approved
0.7471	Intermediate Similarity	NPD7240	Approved
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7469	Intermediate Similarity	NPD5403	Approved
0.7466	Intermediate Similarity	NPD17	Approved
0.7456	Intermediate Similarity	NPD6959	Discontinued
0.7436	Intermediate Similarity	NPD7033	Discontinued
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7421	Intermediate Similarity	NPD7003	Approved
0.7419	Intermediate Similarity	NPD1607	Approved
0.741	Intermediate Similarity	NPD8455	Phase 2
0.7403	Intermediate Similarity	NPD943	Approved
0.7399	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2438	Suspended
0.7389	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5536	Phase 2
0.7368	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1933	Approved
0.7346	Intermediate Similarity	NPD5401	Approved
0.7346	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2344	Approved
0.7342	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7440	Discontinued
0.7325	Intermediate Similarity	NPD2799	Discontinued
0.732	Intermediate Similarity	NPD7095	Approved
0.731	Intermediate Similarity	NPD7229	Phase 3
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3620	Phase 2
0.729	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7285	Intermediate Similarity	NPD2797	Approved
0.7278	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD2354	Approved
0.7267	Intermediate Similarity	NPD3887	Approved
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7255	Intermediate Similarity	NPD6832	Phase 2
0.7251	Intermediate Similarity	NPD1247	Approved
0.7226	Intermediate Similarity	NPD4062	Phase 3
0.7222	Intermediate Similarity	NPD5283	Phase 1
0.7219	Intermediate Similarity	NPD1283	Approved
0.7215	Intermediate Similarity	NPD3748	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7205	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD228	Approved
0.7202	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3972	Approved
0.7197	Intermediate Similarity	NPD6653	Approved
0.719	Intermediate Similarity	NPD2861	Phase 2
0.7186	Intermediate Similarity	NPD6873	Phase 2
0.7181	Intermediate Similarity	NPD7680	Approved
0.7179	Intermediate Similarity	NPD2979	Phase 3
0.7176	Intermediate Similarity	NPD6971	Discontinued
0.7171	Intermediate Similarity	NPD1203	Approved
0.7162	Intermediate Similarity	NPD9268	Approved
0.7161	Intermediate Similarity	NPD2313	Discontinued
0.716	Intermediate Similarity	NPD2309	Approved
0.7152	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD7097	Phase 1
0.7151	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD7177	Discontinued
0.7134	Intermediate Similarity	NPD3146	Approved
0.7134	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3705	Approved
0.7126	Intermediate Similarity	NPD7028	Phase 2
0.7125	Intermediate Similarity	NPD6004	Phase 3
0.7125	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2346	Discontinued
0.7125	Intermediate Similarity	NPD6002	Phase 3
0.7125	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6005	Phase 3
0.7124	Intermediate Similarity	NPD2798	Approved
0.7124	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1876	Approved
0.7099	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1481	Phase 2
0.7081	Intermediate Similarity	NPD5958	Discontinued
0.7073	Intermediate Similarity	NPD4357	Discontinued
0.7063	Intermediate Similarity	NPD5406	Approved
0.7063	Intermediate Similarity	NPD5404	Approved
0.7063	Intermediate Similarity	NPD5405	Approved
0.7063	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5977	Approved
0.7059	Intermediate Similarity	NPD5978	Approved
0.7051	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3751	Discontinued
0.7045	Intermediate Similarity	NPD2163	Approved
0.7043	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7549	Discontinued
0.7037	Intermediate Similarity	NPD1243	Approved
0.703	Intermediate Similarity	NPD642	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